JP6443915B2 - Fluoroalkane derivative, gelling agent, liquid crystalline compound and gel composition - Google Patents

Description

  The present invention relates to a fluoroalkane derivative, a gelling agent, a liquid crystal compound, and a gel composition.

  Conventionally, in various industrial fields (for example, paints, cosmetics, pharmaceutical medicine, oil spill treatment, electronic / optical fields, environmental fields, etc.), liquid substances are solidified, that is, solidified into a jelly or thickened. A gelling agent is used for the purpose.

  These gelling agents include those that gel (solidify) water, and those that gel (solidify) non-aqueous solvents and solutions mainly containing them. The structure of the gelling agent can be roughly classified into a high molecular weight type and a low molecular weight type. The high molecular weight type gelling agent is mainly used for gelation of non-aqueous solvents, and it is characterized by keeping oil solid while taking in oils in the entangled molecule of lipophilic polymer. And On the other hand, many low molecular weight type gelling agents contain hydrogen-bonding functional groups (for example, amino groups, amide groups, and urea groups) in the molecule, and water and non-aqueous solvents are gelated by hydrogen bonds. (For example, refer patent document 1). The low molecular weight type gelling agent is generally used as a water gelling agent, but its development as a nonaqueous solvent gelling agent has been relatively delayed.

  Furthermore, although low molecular weight type gelling agents having no hydrogen bonding group are disclosed in, for example, Patent Document 2 and Non-Patent Document 1, there are very few examples.

  Apart from that, new liquid crystalline compounds are being developed in recent years.

JP-A-8-231942 International Publication No. 2009/78268

J. et al. Fluorine. Chem. 110, 47-58 (2001)

  Therefore, the present invention has been made in view of the above circumstances, and comprises a novel fluoroalkane derivative, a gelling agent comprising the compound, a gel composition containing the gelling agent, and a novel fluoroalkane derivative. An object is to provide a liquid crystal compound.

  When the present inventors diligently examined a novel compound useful as a low molecular weight type gelling agent, it was found that a fluoroalkane derivative having a specific chemical structure acts as a gelling agent. The present inventors have also found that such a fluoroalkane derivative has liquid crystallinity.

That is, the present invention is as follows.
[1] A fluoroalkane derivative represented by the following general formula (1).
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
(In the formula, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic group having 6 to 30 nucleus atoms, and R ¹ is a saturated or unsaturated carbon atom having 1 to 20 carbon atoms. R represents a divalent hydrocarbon group, R represents a group represented by the following general formula (2) , X represents a group represented by —S— or —SO ₂ —, Y represents a cyano group, a nitro group Represents a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms or a fluorine atom.
C _m F _{2m + 1} C _p H _2p − (2)
(In the formula, m represents a natural number of 2 to 16, and p represents an integer of 0 to 6. )
[2 ] A fluoroalkane derivative represented by the following general formula (1).
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
(In the formula, Ar ¹ and Ar ² are each independently a condensed ring having one or more aromatic hydrocarbon rings, or a group in which a plurality of aromatic rings are bonded by a single bond, 1 or more of them represents a group which is an aromatic hydrocarbon ring, and R ¹ is a saturated or unsaturated divalent hydrocarbon having 1 to 20 carbon atoms which may have an oxygen atom or a sulfur atom in the chain. R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms having a perfluoroalkyl group, X represents a group represented by —S— or —SO ₂ —, Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom.)
[3] The fluoroalkane derivative according to claim 2, wherein R is a group represented by the following general formula (2).
C _m F _{2m + 1} C _p H _2p − (2)
(In the formula, m represents a natural number of 2 to 16, and p represents an integer of 0 to 6.)
[4] The fluoroalkane derivative according to any one of [1] to [ 3 ] , wherein Ar ¹ and Ar ² are each independently a phenylene group or a biphenylene group.
[5] A gelling agent comprising a fluoroalkane derivative represented by the following general formula (1) .
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
(In the formula, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic group having 6 to 30 nuclear atoms, and R ¹ has an oxygen atom or a sulfur atom in the chain. A saturated or unsaturated divalent hydrocarbon group having 1 to 20 carbon atoms which may be substituted, and R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms having a perfluoroalkyl group; X represents a group represented by —S— or —SO ₂ —, and Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom. )
[6] A liquid crystalline compound comprising a fluoroalkane derivative represented by the following general formula (1) .
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
(In the formula, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic group having 6 to 30 nuclear atoms, and R ¹ has an oxygen atom or a sulfur atom in the chain. A saturated or unsaturated divalent hydrocarbon group having 1 to 20 carbon atoms which may be substituted, and R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms having a perfluoroalkyl group; X represents a group represented by —S— or —SO ₂ —, and Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom. )
[7] A gel composition containing the gelling agent according to [5] and an organic solvent.

  According to the present invention, a novel fluoroalkane derivative, a gelling agent comprising the compound, a gel composition containing the gelling agent, and a liquid crystalline compound comprising the novel fluoroalkane derivative can be provided.

It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (1-6)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (1-12)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (2)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (1-4)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (3-4)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (3-6)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (5)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (5)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (6)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (6)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (6)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (7)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (8)) of this invention. It is a figure which shows the result of the sol-gel transition temperature for every density | concentration in the organic solvent about the fluoroalkane derivative (compound (9)) of this invention. It is a figure which shows the phase transition temperature at the time of changing the composition ratio of each component in the binary mixture containing the fluoro alkane derivative of this invention. It is a figure which shows the phase transition temperature at the time of changing the composition ratio of each component in the binary mixture containing the fluoro alkane derivative of this invention. It is a figure which shows the phase transition temperature at the time of changing the composition ratio of each component in the binary mixture containing the fluoro alkane derivative of this invention. It is a polarizing microscope photograph of the fluoroalkane derivative of the present invention. It is a polarizing microscope photograph of the fluoroalkane derivative of the present invention. It is a polarizing microscope photograph of the binary mixture containing the fluoroalkane derivative of the present invention.

  Hereinafter, a mode for carrying out the present invention (hereinafter simply referred to as “the present embodiment”) will be described in detail with reference to the drawings as necessary. However, the present invention is limited to the following embodiment. It is not a thing. The present invention can be variously modified without departing from the gist thereof.

The fluoroalkane derivative of this embodiment is represented by the following general formula (1) (hereinafter, this fluoroalkane derivative is also referred to as “compound (1)”).
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
Here, in formula (1), Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic group having 6 to 30 nuclear atoms, and R ¹ is saturated or unsaturated carbon. R represents a divalent hydrocarbon group having 1 to 20 carbon atoms, R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms having a perfluoroalkyl group, and X represents -S- or -SO. ₂ represents a group represented by-, and Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom. Hereinafter, the fluoroalkane derivative of this embodiment will be described in detail.

In the above formula (1), Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic group having 6 to 30 nuclear atoms. Ar ¹ and Ar ² may be the same as or different from each other. The divalent aromatic group is a cyclic divalent group exhibiting so-called “aromaticity”. This divalent aromatic group may be a monocyclic group or a heterocyclic group. The divalent aromatic group may be substituted with a substituent or may be an unsubstituted one that is not substituted. The substituent may be selected from the viewpoint of optimizing the melting point, gelling ability, and liquid crystallinity of the compound (1).

  The monocyclic group has 6-30 ring-forming atoms, may be substituted with a substituent, or may be unsubstituted or unsubstituted. Specific examples thereof include, but are not limited to, a divalent group having a ring represented by a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthranylene group, a phenanthrylene group, a pyrenylene group, a chrysenylene group, or a fluoranthenylene group. The group of is mentioned. Further, the monocyclic group may have two or more of the above-described divalent groups within the range of 6 to 30 ring-forming atoms. Here, two or more divalent groups may be the same as or different from each other. When using a monocyclic group, from the viewpoint of ease of synthesis and ease of gelation, a substituted or unsubstituted phenylene group, biphenylene group, terphenylene group, naphthylene group, and anthranylene group may be used. Preferably, any one of a substituted or unsubstituted phenylene group, biphenylene group, and naphthylene group is used, and any one of a substituted or unsubstituted phenylene group or biphenylene group is more preferably used.

  The heterocyclic group has 6 to 30 ring-forming atoms and is not limited to the following, and examples thereof include a divalent group having a ring represented by a pyridylene group and a pyrimidylene group. Further, the heterocyclic group may have two or more of the above-described divalent groups within the range of 6 to 30 ring-forming atoms. Here, two or more divalent groups may be the same as or different from each other.

Further, Ar ¹ and Ar ² may be a group having both the monocyclic group and the heterocyclic group within the range of 6 to 30 ring-forming atoms.

Among these, Ar ¹ and Ar ² are each independently one or more from the viewpoint of more effectively and reliably having the gelability and the thermal stability or liquid crystallinity of the gel composition containing the compound (1). A condensed ring having an aromatic hydrocarbon ring or a group in which a plurality of aromatic rings are bonded by a single bond, and at least one of the aromatic rings is preferably a group having an aromatic hydrocarbon ring. Moreover, it is more preferable that the plurality of aromatic rings are all aromatic hydrocarbon groups. Examples of such a divalent aromatic group include a biphenylene group, a terphenylene group, a naphthylene group, and an anthranylene group.

In addition to the above, Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenylene group, biphenylene group, terphenylene group, from the viewpoint of easy acquisition of raw materials and easy synthesis. A naphthylene group or an anthranylene group is preferable, a substituted or unsubstituted phenylene group, a biphenylene group, or a naphthylene group is more preferable, and a substituted or unsubstituted phenylene group or a biphenylene group is further preferable. From the viewpoint of easy availability of raw materials and easy synthesis, a phenylene group is preferable, and a biphenylene group is preferable from the viewpoint of showing high gelling ability with a small amount of use.

  Moreover, as said substituent, although not limited to the following, For example, the alkyl group represented by the methyl group and the ethyl group, and a halogen atom are mentioned.

Ar ¹ and Ar ² mainly take into account the gelling ability to be sought (the amount of compound (1) necessary for gelation, the heating temperature necessary to dissolve compound (1) in a solvent), or liquid crystallinity. Selected.

R ¹ represents a saturated or unsaturated divalent hydrocarbon group having 1 to 20 carbon atoms. When the carbon number of R ¹ is 20 or less, the gelation ability of the compound (1) increases and the melting point also increases. On the other hand, when R ¹ has 1 or more carbon atoms, the liquid crystallinity is more excellent. Here, the hydrocarbon group in R ¹ may have not only a carbon atom but also an oxygen atom or a sulfur atom in the chain (preferably in the main chain). R ¹ may be a divalent aliphatic hydrocarbon group, and may further have a monovalent aromatic hydrocarbon group such as a phenyl group as a substituent. When the divalent hydrocarbon group is a divalent aliphatic hydrocarbon group, it may be branched or unbranched (straight). When the divalent hydrocarbon group has a monovalent aromatic hydrocarbon group as a substituent, the aromatic hydrocarbon group may or may not have a substituent.

  Examples of the unsubstituted divalent hydrocarbon group include, but are not limited to, branched or straight chain having 1 to 6 carbon atoms such as a methylene group, an ethylene group, a propylene group, an n-butylene group, and an isobutylene group. Oxyalkylene groups such as alkylene groups, oxymethylene groups, oxyethylene groups, oxypropylene groups, oxydimethylene groups, oxydiethylene groups and oxydipropylene groups, thiomethylene groups, thioethylene groups, thiopropylene groups, thiodimethylene groups, thiodiethylenes Groups and thioalkylene groups such as thiodipropylene groups.

R ¹ is independently preferably a divalent hydrocarbon group having 2 to 16 carbon atoms, and more preferably a divalent hydrocarbon group having 4 to 12 carbon atoms. R ¹ is preferably an alkylene group, and more preferably an alkylene group having 4 to 12 carbon atoms. When R ¹ is as described above, a compound (1) having a higher gelation ability can be obtained by a synthetic route in which raw materials are more easily available. Furthermore, the more the carbon number of R ¹ is within the above range, the higher the gelability and the thermal stability of the gel composition containing the compound (1).

  R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms having a perfluoroalkyl group. The number of carbons in the main chain of R is preferably 4 to 16, and more preferably 4 to 10. By making the carbon number within the above range, the compound (1) becomes a compound that is easier to synthesize, exhibits higher gelation ability, and is more excellent in handleability.

R preferably contains a perfluoroalkyl group (hereinafter referred to as “Rf group” in this paragraph) and an alkylene group (hereinafter referred to as “Rh group” in this paragraph), and consists of them. It is more preferable that Specifically, R is preferably a group represented by the following general formula (2).
C _m F _{2m + 1} C _p H _2p − (2)
Here, in formula (2), m represents a natural number of 2 to 16, and p represents an integer of 0 to 6.

  From the same viewpoint, from the viewpoint of handleability and ease of synthesis, m is preferably 2 to 10, and more preferably 4 to 8. From the same viewpoint, p is preferably 2 to 6, and more preferably 2 to 4. Further, m is preferably larger than p, and the Rf group is more preferably a straight chain structure without branching. The chain of the Rf group greatly affects the gelling ability.

X represents a sulfur atom (a group represented by —S—) or an SO ₂ group (a group represented by —SO ₂ —). When the compound (1) has these divalent groups, the balance between handleability and gelling ability or liquid crystallinity is excellent. When the compound (1) has a sulfur atom, it is excellent in handleability and is further easily synthesized. On the other hand, when the compound (1) has an SO ₂ group, the gelation performance or liquid crystallinity is further improved.

  Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom. The saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms is preferably a saturated or unsaturated monovalent alkoxy group having 2 to 10 carbon atoms, and saturated monovalent alkoxy having 2 to 8 carbon atoms. Groups are more preferred. When Y is a cyano group or a nitro group, the compound (1) becomes more excellent in liquid crystallinity, and when Y is a monovalent alkoxy group having 2 to 20 carbon atoms or a fluorine atom, gelation ability and The thermal stability of the gel composition containing the compound (1) is improved.

Hereinafter, preferable examples of the compound (1) of the present embodiment are exemplified as combinations of R, X, Ar ¹ , R ¹ , Ar ² and Y.

  Although the manufacturing method of the compound (1) of this embodiment is not specifically limited, For example, it is compoundable with the following scheme or the scheme according to it. In more detail, it can be synthesized by the method described in the examples. Moreover, the code | symbol same as the said General formula (1) among the code | symbols in each formula is synonymous with the thing in the general formula (1), and when each formula has the same code | symbol mutually, those code | symbols mutually It is synonymous.

First, a compound represented by the following general formula (1a) is sulfided with a compound represented by the following general formula (1b) in the presence of an alkali metal compound such as K ₂ CO _{3 in} a solvent such as acetone. A compound represented by the following general formula (1c) is obtained.
H—S—Ar ¹ —OH (1a)
RZ ¹ (1b)
R—S—Ar ¹ —OH (1c)
Here, in the above formula, Z ¹ represents a halogen atom such as an iodine atom (the same applies hereinafter).

Next, the compound represented by the general formula (1c) is a compound represented by the following general formula (1d) in the presence of an alkali metal compound such as K ₂ CO _{3 in} a solvent such as acetone or 3-pentanone. Etherification yields a compound represented by the following general formula (1e).
Z ² -R ¹ -Z ² (1d)
R—S—Ar ¹ —O—R ¹ —Z ² (1e)
Here, in the formulas (1d) and (1e), Z ² represents a halogen atom such as a bromine atom (the same applies hereinafter).

By oxidizing (sulfonylating) the compound represented by the general formula (1e) with an oxidizing agent such as hydrogen peroxide in the presence of a catalyst such as acetic acid, the compound represented by the following general formula (1f) is obtained. can get.
R—SO ₂ —Ar ¹ —O—R ¹ —Z ² (1f)

Next, the compound represented by the above formula (1e) or (1f) is represented by the following general formula (1g) in the presence of an alkali metal compound such as K ₂ CO _{3 in} a solvent such as acetone, 3-pentanone or cyclohexanone. Reaction with the represented compound gives compound (1).
HO—Ar ² —Y (1 g)

Further, when Ar ¹ is a group in which a plurality of aromatic rings such as a biphenylene group, a terphenylene group, or a phenylenepyridylene group are bonded by a single bond, the compound (1) can be obtained by, for example, the following synthesis method. First, a thiol compound represented by the following general formula (1h) is sulfided with a compound represented by the above general formula (1b) in the presence of an alkali metal compound such as K ₂ CO _{3 in} a solvent such as acetone. The compound represented by the following general formula (1i) is obtained. Here, in the formulas (1h) and (1i), Z ³ represents a halogen atom such as a bromine atom, and Ar ³ is a divalent aromatic hydrocarbon constituting Ar ¹ in the general formula (1). A part of the group is shown.
^{HS-Ar 3 -Z 3 (1h} )
R—S—Ar ³ —Z ³ (1i)

Next, the following compound (1j) is obtained by oxidizing the compound represented by the general formula (1i) with an oxidizing agent such as hydrogen peroxide in the presence of a catalyst such as acetic acid.
R—SO ₂ —Ar ³ —Z ³ (1j)

Next, from the compound represented by the general formula (1i) or (1j) and the compound represented by the following general formula (1k), in the presence of a palladium catalyst in an aqueous base solution such as Na ₂ CO ₃ , A compound represented by the following general formula (1l) is obtained by Suzuki-Miyaura coupling. Here, in the formula (1k), Ar ⁴ represents a part of the divalent aromatic hydrocarbon group constituting Ar ¹ in the general formula (1), and represents a part different from Ar ^3. Ar ³ and Ar ⁴ are bonded by a single bond to form Ar ¹ . R ² represents an alkyl group such as a methyl group.
R ² —O—Ar ³ —B (OH) ₂ (1k)
R—X—Ar ¹ —O—R ² (1 l)

Next, the compound represented by the general formula (1l) is dealkylated in the presence of an acid catalyst to obtain a compound represented by the following general formula (1m).
R—X—Ar ¹ —OH (1 m)

Next, the compound represented by the general formula (1m) is converted into the compound represented by the general formula (1d) in a solvent such as acetone or 3-pentanone in the presence of an alkali metal compound such as K ₂ CO ₃ . To obtain a compound represented by the following general formula (1n).
R—X—Ar ¹ —O—R ¹ —Z ² (1n)

Then, the compound represented by the above formula (1n) is converted to the compound represented by the above general formula (1g) in the presence of an alkali metal compound such as K ₂ CO _{3 in} a solvent such as acetone, 3-pentanone or cyclohexanone. To give compound (1).

  The compound (1) of this embodiment can be used as a gelling agent that gels an organic solvent. In particular, such a compound is advantageous in that it can be gelled or solidified by adding a small amount of various organic solvents. Moreover, the gel-like composition of this embodiment contains 1 type, or 2 or more types of compounds (1), and an organic solvent.

  The organic solvent contained in the gel composition of the present embodiment is preferably a non-aqueous solvent. The non-aqueous solvent is not particularly limited, but a non-aqueous solvent that is liquid at room temperature is generally used.

  Examples of such non-aqueous solvents include alcohols such as methanol, ethanol, isopropanol, butanol and octanol, methyl acetate, ethyl acetate, propyl acetate, butyl acetate and γ-butyrolactone, γ-valerolactone, ε-caprolactone, etc. Acid esters, ketones such as dimethyl ketone, diethyl ketone, methyl ethyl ketone, 3-pentanone and acetone, fluorine such as pentane, hexane, octane, cyclohexane, perfluorodecalin, benzene, toluene, xylene, fluorobenzene and hexafluorobenzene Hydrocarbons which may have an atom, diethyl ether, 1,2-dimethoxyethane, 1,4-dioxane, crown ethers, glymes, tetrahydrofuran and fluoroalkyl ether Ethers such as N, N-dimethylacetamide, N, N-dimethylformamide, amides such as ethylenediamine and pyridine, carbonates such as propylene carbonate, ethylene carbonate, vinylene carbonate, fluoroethylene carbonate, diethyl carbonate, ethyl methyl carbonate , Amines which may have a fluorine atom such as perfluorotributylamine, nitriles such as acetonitrile, propionitrile, adiponitrile and methoxyacetonitrile, lactams such as N-methylpyrrolidone (NMP), sulfolane and the like Examples include sulfones, sulfoxides such as dimethyl sulfoxide, industrial oils such as silicon oil and petroleum, and edible oils.

  Moreover, an ionic liquid can also be used as a non-aqueous solvent. An ionic liquid is a room temperature molten salt composed of ions obtained by combining an organic cation and an anion. Ionic liquids are flame retardant, have low explosive properties, and have almost no vapor pressure. In addition, ionic liquids have high heat and ion conductivity, physical property control design is possible by selecting ionic species, and selective and high gas absorption capability, so that they can be used in various applications. Is expected.

  Examples of organic cations include imidazolium ions such as dialkylimidazolium cations and trialkylimidazolium cations, tetraalkylammonium ions, trialkylalkoxyalkylammonium ions, alkylpyridinium ions, dialkylpyrrolidinium ions, and dialkylpiperidinium ions. It is done.

Examples of the anion serving as a counter for these organic cations include PF ₆ anion, PF ₃ (C ₂ F ₅ ) ₃ anion, PF ₃ (CF ₃ ) ₃ anion, BF ₄ anion, and BF ₂ (CF ₃ ) ₂ anion. , BF ₃ (CF ₃ ) anion, bisoxalatoborate anion, Tf (trifluoromethanesulfonyl) anion, Nf (nonafluorobutanesulfonyl) anion, bis (fluorosulfonyl) imide anion, bis (trifluoromethanesulfonyl) imide anion, bis (Pentafluoroethanesulfonyl) imide anion, dicyanoamine anion, halide anion and the like can be used.

  These non-aqueous solvents are used alone or in combination of two or more.

  The gel composition of the present embodiment preferably contains 0.05 to 10.0% by mass of compound (1), more preferably 0.1 to 8.0% by mass, and 0.3 More preferably, the content is ˜5.0 mass%. When the content is equal to or higher than the lower limit, the compound (1) tends to function more satisfactorily as a gelling agent. When the content is equal to or lower than the upper limit, the economy and handling properties tend to be further improved. In addition, it is possible to further suppress the gelling agent from becoming an impurity and further prevent the performance of the nonaqueous solvent from being deteriorated. From the same viewpoint, the gel composition of the present embodiment preferably contains 90 to 99.95% by mass of the organic solvent, more preferably 92 to 99.9% by mass, and more preferably 95 to 99.99% by mass with respect to the total amount. More preferably, the content is 7% by mass.

  The gel composition of this embodiment may contain other components in addition to the compound (1) and the organic solvent as long as the function of the compound (1) as a gelling agent is not inhibited. Examples of such components include gelling agents other than compound (1), coagulants, thickeners, stabilizers, antioxidants, emulsifiers, lubricants, and safety improving additives.

  Although the preparation method of the gel composition of this embodiment is not specifically limited, For example, it mixes, heating an organic solvent, a gelatinizer (namely, compound (1)), and other additives, etc. to a uniform liquid mixture. Then, it can be prepared by lowering the temperature of the mixture. The order of mixing the components is not particularly limited, but it is preferable to prepare a solution composed of a non-aqueous solvent and an additive in advance and then mix the gelling agent, so that a uniform mixed solution can be obtained more easily.

  Moreover, the compound (1) of this embodiment can also be used as a liquid crystalline compound. Compound (1) can form a smectic A phase in a specific temperature range.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples. Hereinafter, the compounds represented by the general formula (α), the general formula (α-β), and the general formula (γ) (α and β represent natural numbers, and γ represents an alphabet) are respectively represented by the compounds ( α), compound (α-β) and compound (γ). The same applies to the brief description of the drawings.

Example 1
(Synthesis of Compound (1-6))
First, a compound represented by the following formula (A) was obtained by the following scheme.

Specifically, first, 2- (perfluorohexyl) ethyl iodide 21.70 g (45.8 mmol), 4-mercaptophenol 5.72 g (45.3 mmol), potassium carbonate 7.24 g (52.8 mmol), and 50 mL of acetone was placed in a 200 mL eggplant flask and refluxed at 65 ° C. for 2 days. After completion of the reaction, the mixture was allowed to stand at room temperature and transferred to a separatory funnel. An appropriate amount of water and 30 mL of 1N hydrochloric acid were added thereto, and then ethyl acetate and brine were further added to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, followed by pleat filtration, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 18.23 g (38.6 mmol) of compound (A). The obtained compound (A) was a colorless powder, its melting point was 65 to 68 ° C., and the yield was 85.2%. In addition, an infrared spectrophotometer (manufactured by Shimadzu Corporation, trade name “IR Prestige-21”, the same applies hereinafter) and a nuclear magnetic resonance apparatus (manufactured by JEOL Ltd., trade name “JMN-LA500”). The same shall apply hereinafter) to identify the compound (A). The results are shown below.
IR (KBr): ν = 3431 (OH), 1588,1492 (C = C), 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 2.28-2.38 (2H, m), 2.99 (2H, tt, J = 8.2, 2.7 Hz), 5.00 (1H, s), 6.82 (2H, d, J = 8.5 Hz), 7.34 (2H, d, J = 8.5 Hz) ppm

Next, the compound (B) was obtained according to the following scheme.

Specifically, first, 2.12 g (4.47 mmol) of compound (A), 3.68 g (15.1 mmol) of 1,6-dibromohexane, 0.72 g (5.22 mmol) of potassium carbonate, and 50 mL of acetone were added. The flask was placed in a 200 mL eggplant flask and refluxed at 60 ° C. for 11 hours. Meanwhile, the progress of the reaction was confirmed every hour by high performance liquid chromatography (HPLC). After completion of the reaction, the mixture was allowed to stand at room temperature and transferred to a separatory funnel. Water, ethyl acetate and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, followed by pleat filtration, and the filtrate was concentrated with an evaporator to obtain a liquid. Methanol was added to the obtained liquid, the precipitated solid was filtered off, and the obtained filtrate was distilled under reduced pressure to obtain 1.79 g (2.81 mmol) of Compound (B). The obtained compound (B) was a gray solid, its melting point was 35 to 37 ° C., and the yield was 62.9%. Moreover, the compound (B) was identified with the infrared spectrophotometer and the nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1591, 1496 (C = C), 1235-1140 (CF), 640-520 (C-Br) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.49-1.58 (6H, m), 1.80 (2H, quin, J = 6.4 Hz), 1.90 (2H, quin, J = 6.4 Hz), 2.28-2.38 (2H , m), 3.30 (2H, tt, J = 7.9, 3.1 Hz), 3.42 (2H, t, J = 6.7 Hz), 3.95 (2H, t, J = 6.7 Hz), 6.86 (2H, d, J = 8.5 Hz), 7.36 (2H, d, J = 8.5 Hz) ppm

And the compound (1-6) was obtained with the following scheme.

Specifically, first, 1.8 g (2.38 mmol) of compound (B), 0.59 g (2.40 mmol) of 4-cyano-4′-hydroxybiphenyl, 0.53 g (3.89 mmol) of potassium carbonate, and 50 mL of acetone was placed in a recovery flask and refluxed at 65 ° C. for 2 days. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 1.49 g (1.99 mmol) of compound (1-6). The obtained compound (1-6) was a colorless powder, its melting point was 108 to 110 ° C., and the yield was 83.6%. In addition, compound (1-6) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 2250 (C≡N), 1593,1491 (C = C), 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.56 (4H, quin, J = 3.66 Hz), 1.85 (4H, quin, J = 4.12 Hz), 2.28-2.38 (2H, m), 3.00 (2H, tt , J = 7.9, 3.1 Hz), 3.97 (2H, t, J = 6.41 Hz), 4.02 (2H, t, J = 6.41 Hz), 6.87 (2H, d, J = 8.55 Hz), 6.99 (2H, d , J = 8.55 Hz), 7.36 (2H, d, J = 9.16 Hz), 7.52 (2H, d, J = 9.16 Hz), 7.63 (2H, d, J = 8.55 HZ), 7.69 (2H, d, J = 8.55 Hz) ppm

(Example 2)
(Synthesis of Compound (2))
First, compound (C) was obtained according to the following scheme.

Specifically, first, 1.79 g (2.81 mmol) of the compound (B) obtained as described above, 0.29 g (2.91 mmol) of 35% by mass hydrogen peroxide, and 50 mL of acetic acid were added to 200 mL eggplant. The flask was placed in a flask and refluxed at 110 ° C. overnight. After completion of the reaction, the mixture was allowed to stand to room temperature, and 40 mL of 6% by mass sodium bisulfite was added thereto, followed by suction filtration to obtain 1.59 g (2.38 mmol) of Compound (C). The obtained compound (C) was a colorless crystal, the melting point was 64-65 ° C., and the yield was 85%. Moreover, the compound (C) was identified with the infrared spectrophotometer and the nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1593,1497 (C = C), 1235-1140 (CF), 640-520 (C-Br) cm ^−1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.52-1.58 (8H, m), 1.85 (2H, quin, J = 6.4 Hz), 1.91 (2H, quin, J = 6.4 Hz), 2.53-2.63 (2H , m), 3.29 (2H, tt, J = 8.5, 4.0 Hz), 3.43 (2H, t, J = 6.7 Hz), 4.06 (2H, t, J = 6.4 Hz), 7.05 (2H, d, J = 8.5 Hz), 7.85 (2H, d, J = 8.5 Hz) ppm

Next, a compound (2) was obtained according to the following scheme.

Specifically, first, 2.60 g (3.89 mmol) of compound (C), 0.76 g of 4-cyano-4′-hydroxybiphenyl, (3.89 mmol), 0.57 g (4.11 mmol) of potassium carbonate, And 50 mL of 3-pentanone was put into a 200 mL eggplant flask and refluxed at 110 ° C. for 24 hours. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, followed by pleat filtration, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform and then recrystallized with ethanol to obtain 2.19 g (2.84 mmol) of Compound (2). The obtained compound (2) was a colorless powder, its melting point was 126 to 128 ° C., and the yield was 73.0%. In addition, Compound (2) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 2235 (C≡N), 1588,1498 (C = C), 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.56 (4H, quin, J = 3.66 Hz), 1.87 (4H, quin, J = 6.71 Hz), 2.28-2.38 (2H, m), 3.00 (2H, tt , J = 8.5, 4.0 Hz), 4.03 (2H, t, J = 6.41 Hz), 4.07 (2H, t, J = 6.41 Hz), 6.99 (2H, d, J = 8.55 Hz), 7.05 (2H, d , J = 9.16 Hz), 7.53 (2H, d, J = 8.55 Hz), 7.64 (2H, d, J = 8.55 Hz), 7.69 (2H, d, J = 8.55 HZ), 7.84 (2H, d, J = 9.16 Hz) ppm

Example 3
(Synthesis of Compound (1-12))
Compound (1-12) was obtained according to the following scheme.

Specifically, first, 3.00 g (6.33 mmol) of compound (A), 3.31 g (9.50 mmol) of 1,12-dibromoundecane, 1.03 g of potassium carbonate (7.46 mmol), and 50 mL of acetone Was placed in a 200 mL eggplant flask and refluxed at 60 ° C. for 11 hours. Meanwhile, the progress of the reaction was confirmed every hour by HPLC. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, ethyl acetate and brine were added thereto to separate into an aqueous phase and an organic phase. Next, after adding anhydrous magnesium sulfate to the organic phase and allowing to stand for 30 minutes, pleat filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. Subsequently, the obtained solid was washed with cyclopentyl methyl ether, suction filtered again, and the washing was further performed twice. 2.00 g of the obtained solid, 1.24 g of 4-cyano-4′-hydroxybiphenyl, (6.36 mmol), 1.24 g of potassium carbonate, (8.99 mmol), and 50 mL of 3-pentanone were placed in an eggplant flask. , And refluxed at 110 ° C. for 2 days. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, ethyl acetate and brine were added thereto to separate into an aqueous phase and an organic phase. Next, after adding anhydrous magnesium sulfate to the organic phase and allowing to stand for 30 minutes, pleat filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by recycle HPLC with chloroform to obtain 0.82 g (0.98 mmol) of compound (1-12). The obtained compound (1-12) was a colorless powder, its melting point was 107 to 108 ° C., and the yield was 15.5%. In addition, compound (1-12) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 2220 (C≡N), 1590,1496 (C = C), 1235-1140 (CF) cm ^−1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.29-1.36 (10H, m), 1.42-1.50 (2H, m), 1.74-1.83 (8H, m), 2.27-2.38 (2H, m), 2.96 ( 2H, tt, J = 7.9, 3.1 Hz), 3.94 (2H, t, J = 6.41 Hz), 4.00 (2H, t, J = 6.71 Hz), 6.86 (2H, d, J = 9.16 Hz), 6.98 ( 2H, d, J = 9.16 Hz), 7.36 (2H, d, J = 9.16 Hz), 7.51 (2H, d, J = 8.55 Hz), 7.62 (2H, d, J = 8.54 Hz), 7.67 (2H, d, J = 9.16 Hz) ppm

(Example 4)
(Synthesis of Compound (1-4))
First, compound (H) was obtained according to the following scheme.

Specifically, first, 3.08 g (6.53 mmol) of compound (A), 4.44 g (20.6 mmol) of 1,4-dibromobutane, 1.50 g (10.9 mmol) of potassium carbonate, and 50 mL of acetone were added. The flask was placed in a 200 mL eggplant flask and refluxed at 60 ° C. for 9 hours. Meanwhile, the progress of the reaction was confirmed every hour by high performance liquid chromatography (HPLC). After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, ethyl acetate and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, followed by pleat filtration, and the filtrate was concentrated with an evaporator to obtain a liquid. Methanol was added to the obtained liquid for recrystallization and suction filtration was performed, and the obtained filtrate was distilled under reduced pressure to obtain 3.12 g (5.12 mmol) of compound (H). The compound (H) obtained was a gray viscous solid, its melting point was 26-30 ° C., and the yield was 78%. Moreover, the compound (H) was identified with the infrared spectrophotometer and the nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1234-1182 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.95 (2H, quin, J = 3.05 Hz) 2.07 (2H, quin, J = 3.05 Hz), 2.28-2.38 (2H, m), 2.99 (2H, tt, J = 8.2, 2.7 Hz), 3.49 (2H, t, J = 6.41 Hz), 3.99 (2H, t, J = 6.10 Hz), 6.86 (2H, d, J = 8.55 HZ), 7.37 (2H, d, J = 8.55 Hz) ppm

And the compound (1-4) was obtained with the following scheme.

Specifically, first, 0.59 g (0.97 mmol) of compound (H), 0.19 g (0.97 mmol) of 4-cyano-4′-hydroxybiphenyl, 0.20 g (1.45 mmol) of potassium carbonate, and 50 mL of 3-pentanone was placed in a 200 mL eggplant flask and refluxed at 110 ° C. for 24 hours. After completion of the reaction, the mixture was allowed to stand at room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 0.52 g (0.72 mmol) of the compound (1-4). The compound (1-4) obtained was a white powder, its melting point was 124-125 ° C., and the yield was 74%. Moreover, the compound (1-4) was identified with the infrared spectrophotometer and the nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 2232 (C≡N), 1235-1140 (CF) cm ^−1
1 H NMR (500 MHz, CDCl ₃ ): δ = 2.00 (4H, quin, J = 3.05 Hz), 2.28-2.38 (2H, m), 3.00 (2H, tt, J = 8.2, 2.7 Hz), 4.04 (2H , t, J = 5.50 Hz), 4.09 (2H, t, J = 5.80 Hz), 6.87 (2H, d, J = 9.16 Hz), 6.99 (2H, d, J = 8.55 Hz), 7.37 (2H, d , J = 8.55 Hz), 7.53 (2H, d, J = 8.55 Hz), 7.63 (2H, d, J = 8.55 HZ), 7.69 (2H, d, J = 8.55 Hz) ppm

(Example 5)
(Synthesis of Compound (3-4))
Compound (3-4) was obtained by the following scheme.

Specifically, first, 0.57 g (0.94 mmol) of compound (H), 0.20 g (0.94 mmol) of 4-hydroxy-4′-nitrobiphenyl, 0.21 g (1.52 mmol) of potassium carbonate, and 50 mL of acetone was placed in a 200 mL eggplant flask and refluxed at 65 ° C. for 2 days. After completion of the reaction, the mixture was allowed to stand at room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 0.51 g (0.69 mmol) of the compound (3-4). The compound (3-4) obtained was a yellow powder, the melting point was 94 to 96 ° C., and the yield was 73%. In addition, compound (3-4) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1530 (NO ₂ ), 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 2.03 (4H, quin, J = 3.05 Hz), 2.28-2.39 (2H, m), 3.00 (2H, tt, J = 8.2, 2.7 Hz), 4.05 (2H , t, J = 5.80 Hz), 4.10 (2H, t, J = 5.80 Hz), 6.88 (2H, d, J = 8.55 Hz), 7.01 (2H, d, J = 9.16 Hz), 7.37 (2H, d , J = 8.55 Hz), 7.57 (2H, d, J = 9.16 Hz), 7.68 (2H, d, J = 9.16 HZ), 8.26 (2H, d, J = 9.16 Hz) ppm

(Example 6)
(Synthesis of Compound (3-6))
Compound (3-6) was obtained by the following scheme.

Specifically, first, 0.83 g (1.30 mmol) of compound (B), 0.29 g (1.30 mmol) of 4-hydroxy-4′-nitrobiphenyl, 0.25 g (1.81 mmol) of potassium carbonate, and 50 mL of acetone was placed in a 200 mL eggplant flask and refluxed at 65 ° C. for 2 days. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 0.62 g (0.81 mmol) of compound (3-6). The compound (3-6) obtained was a yellow powder, the melting point was 76 to 78 ° C., and the yield was 62%. In addition, Compound (3-6) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1533 (NO2), 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.56-1.57 (4H, m), 1.85 (4H, quin, J = 4.28 Hz), 2.28-2.38 (2H, m), 2.99 (2H, tt, J = 8.2, 2.7 Hz), 3.98 (2H, t, J = 6.41 Hz), 4.03 (2H, t, J = 6.41 Hz), 6.87 (2H, d, J = 8.55 Hz), 7.01 (2H, d, J = 8.55 Hz), 7.37 (2H, d, J = 9.16 Hz), 7.57 (2H, d, J = 9.16 Hz), 7.68 (2H, d, J = 8.55 HZ), 8.26 (2H, d, J = 9.16 Hz) ) ppm

(Example 7)
(Synthesis of Compound (4-4))
Compound (4-4) was obtained by the following scheme.

Specifically, first, 0.76 g (1.24 mmol) of compound (H), 0.14 g (1.24 mmol) of 4-cyanophenol, 0.25 g (1.81 mmol) of potassium carbonate, and 50 mL of acetone were added to 200 mL eggplant. The flask was placed in a flask and refluxed at 65 ° C. for 2 days. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 0.35 g (0.54 mmol) of the compound (4-4). The compound (4-4) obtained was a white powder, the melting point was 67-69 ° C., and the yield was 44%. In addition, Compound (4-4) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 2228 (C≡N), 1235-1140 (CF) cm ^−1
1 H NMR (500 MHz, CDCl ₃ ): δ = 2.00 (4H, quin, J = 2.59), 2.28-2.38 (2H, m), 3.00 (2H, tt, J = 8.2, 2.7 Hz), 4.03 (2H, t, J = 5.80 Hz), 4.08 (2H, t, J = 5.80 Hz), 6.86 (2H, d, J = 9.16 Hz), 6.93 (2H, d, J = 8.55 Hz), 7.37 (2H, d, J = 8.55 HZ), 7.58 (2H, d, J = 9.16 Hz) ppm

(Example 8)
(Synthesis of Compound (4-6))
Compound (4-6) was obtained by the following scheme.

Specifically, first, 0.94 g (1.48 mmol) of compound (B), 0.18 g (1.48 mmol) of 4-cyanophenol, 0.25 g (1.81 mmol) of potassium carbonate, and 50 mL of acetone were added to 200 mL eggplant. The flask was placed in a flask and refluxed at 65 ° C. for 2 days. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 0.48 g (0.71 mmol) of the compound (4-6). The compound (4-6) obtained was a white powder, the melting point was 68 to 70 ° C., and the yield was 48%. In addition, Compound (4-6) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 2223 (C≡N), 1235-1140 (CF) cm ^−1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.55 (4H, quin, J = 3.66 Hz), 1.80-1.87 (4H, m), 2.28-2.38 (2H, m), 2.99 (2H, tt, J = 8.2, 2.7 Hz), 3.97 (2H, t, J = 6.41 Hz), 4.01 (2H, t, J = 6.41 Hz), 6.86 (2H, d, J = 8.55 Hz), 6.93 (2H, d, J = 8.55 Hz), 7.37 (2H, d, J = 8.55 HZ), 7.57 (2H, d, J = 9.16 Hz) ppm

Example 9
(Synthesis of Compound (5))
Compound (5) was obtained by the following scheme.

Specifically, first, 0.94 g (1.48 mmol) of compound (B), 0.27 g (0.97 mmol) of 4-hydroxy-4′-hexylbiphenyl, 0.18 g (1.30 mmol) of potassium carbonate, and 50 mL of 3-pentanone was placed in a 200 mL eggplant flask and refluxed at 110 ° C. for 12 hours. After completion of the reaction, the mixture was allowed to stand at room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by recycle HPLC with chloroform to obtain 0.45 g (0.55 mmol) of Compound (5). The compound (5) obtained was a white powder, its melting point was 142-144 ° C., and the yield was 57%. In addition, Compound (5) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 0.90-0.93 (3H, m), 1.33-1.36 (4H, m), 1.47 (2H, quin, J = 7.25 Hz), 1.55-1.63 (4H, m) , 1.77-1.85 (6H, m), 2.28-2.38 (2H, m), 2.99 (2H, tt, J = 8.2, 2.7 Hz), 3.99 (6H, ttt, J = 6.41, 6.41, 6.41 Hz), 6.87 (2H, d, J = 8.55 Hz), 6.93 (4H, dd, J = 8.55, 8.55 Hz), 7.36 (2H, d, J = 9.16 Hz), 7.46 (4H, dd, J = 8.55, 8.55 Hz) ppm

(Example 10)
(Synthesis of Compound (6))
Compound (6) was obtained by the following scheme.

Specifically, first, compound (B) 0.60 g (0.94 mmol), 4-fluoro-4′-hydroxybiphenyl 0.18 g (0.94 mmol), potassium carbonate 0.18 g (1.30 mmol), and 50 mL of acetone was placed in a 200 mL eggplant flask and refluxed at 65 ° C. for 2 days. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by recycle HPLC with chloroform to obtain 0.35 g (0.47 mmol) of Compound (6). The compound (6) obtained was a white powder, its melting point was 115 to 117 ° C., and the yield was 51%. In addition, compound (6) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.55-1.57 (4H, m), 1.84 (4H, quin, J = 5.04 Hz), 2.28-2.38 (2H, m), 2.99 (2H, tt, J = 8.2, 2.7 Hz), 3.97 (2H, t, J = 6.41 Hz), 4.01 (2H, t, J = 6.41 Hz), 6.87 (2H, d, J = 9.16 Hz), 6.95 (2H, d, J = 9.16 Hz), 7.09 (2H, dd, J = 8.55, 9.16 Hz), 7.36 (2H, d, J = 8.55 Hz), 7.45 (2H, d, J = 8.5 Hz), 7.49 (2H, dd, J = (9.2, 5.5) ppm

(Example 11)
(Synthesis of Compound (7))
First, compound (D) was obtained according to the following scheme.

Specifically, first, 4.62 g (9.75 mmol) of 2- (perfluorohexyl) ethyl iodide, 1.81 g (9.57 mmol) of 4-bromobenzene teal, 1.51 g (10.9 mmol) of potassium carbonate, And 50 mL of acetone was put into a 200 mL eggplant flask and refluxed at 65 ° C. for 24 hours. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, followed by pleat filtration, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was recrystallized from methanol and filtered with suction to obtain 4.59 g (8.58 mmol) of Compound (D). The obtained compound (D) was a colorless powder, its melting point was 38 to 40 ° C., and the yield was 89.6%. Moreover, the compound (D) was identified with the infrared spectrophotometer and the nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1580, 1477 (C = C), 1248-1140 (CF) cm ^−1
1 H NMR (500 MHz, CDCl ₃ ): δ = 2.33-2.43 (2H, m), 3.10 (2H, tt, J = 8.2, 2.7 Hz), 7.23 (2H, d, J = 8.5 Hz), 7.46 (2H , d, J = 8.5 Hz) ppm

Next, a compound (E) was obtained according to the following scheme.

Specifically, first, 5.01 g (2.68 mmol) of 4-bromoanisole, 0.82 g (33.7 mmol) of shaped magnesium and 25 mL of dry tetrahydrofuran were placed in a 200 mL two-necked flask under a nitrogen atmosphere, The mixture was stirred until a gray solution was obtained. Next, after cooling to −78 ° C., 3.43 g (3.30 mmol) of trimethyl borate and 15 mL of dry tetrahydrofuran were added thereto and stirred for 2 hours. Thereafter, the mixture was gradually returned to room temperature and further stirred for 2 hours. Subsequently, it was made into air atmosphere, 50 mL of 1N dilute hydrochloric acid was added in ice cooling, and it stirred for 1 hour. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Thereto, ethyl acetate, water and brine were further added to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, followed by pleat filtration, and the filtrate was concentrated with an evaporator to obtain 2.63 g (17.3 mmol) of Compound (E). The obtained compound (E) was a gray powder, its melting point was 201 to 206 ° C., and the yield was 65.0%. Moreover, the compound (E) was identified with the infrared spectrophotometer and the nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 3358 (OH), 1601, 1580 (C = C), 1250 (> O) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 3.76 (3H, s), 6.88 (2H, d, J = 8.5 Hz), 7.73 (2H, d, J = 8.5 Hz), 7.85 (2H, s) ppm

Next, the compound (F) was obtained according to the following scheme.

Specifically, first, under a nitrogen atmosphere, 7.10 g (13.3 mmol) of compound (D), 2.30 g (15.1 mmol) of compound (E), 1.98 g (18.7 mmol) of sodium carbonate, acetic acid Palladium (II) 0.01 g (0.045 mmol), triphenylphosphine 0.03 g (0.11 mmol), water 20 mL and 1,4-dioxane 80 mL were placed in a flask, and refluxed at 100 ° C. for 18 hours. After the completion of the reaction, the mixture was allowed to stand until it reached room temperature, and was neutralized by adding 50 mL of 1N hydrochloric acid, followed by suction filtration to obtain a solid. The solid was dissolved in ethyl acetate, further subjected to suction filtration, and the filtrate was concentrated by an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography to obtain 7.04 g (12.5 mmol) of compound (F). The compound (F) obtained was a brown powder, the melting point was 128 to 131 ° C., and the yield was 94.2%. Moreover, the compound (F) was identified with the infrared spectrophotometer and the nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1601, 1580 (C = C), 1250 (> O), 1248-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 2.33-2.48 (2H, m), 3.14 (2H, tt, J = 8.2, 2.7 Hz), 3.85 (3H, s), 6.98 (2H, d, J = 9.2 Hz), 7.41 (2H, d, J = 8.5 Hz), 7.52 (2H, d, J = 9.2 Hz), 7.52 (2H, d, J = 8.5 Hz) ppm

Next, the compound (G) was obtained according to the following scheme.

Specifically, first, 7.04 g (12.5 mmol) of the compound (F) and 60 mL of dichloromethane were placed in a 500 mL eggplant flask and stirred for 1 hour in an ice bath, and then 8.01 g (31 of boron tribromide) .9 mmol) was added, the temperature was gradually returned to room temperature, and the mixture was further stirred for 12 hours. Next, the atmosphere was changed to air, and water was added in ice-cooling and stirred for 1 hour. The precipitated solid was subjected to suction filtration, and this solid was recrystallized from chloroform to obtain 5.14 g (9.38 mmol) of Compound (G). The obtained compound (G) was a colorless powder, its melting point was 170 to 173 ° C., and the yield was 63.2%. Moreover, the compound (G) was identified with the infrared spectrophotometer and the nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 3445 (OH), 1609, 1489 (C = C), 1235-1186 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 2.43-2.51 (2H, m), 3.16 (2H, tt, J = 8.2, 2.7 Hz), 6.78 (2H, d, J = 8.5 Hz), 7.36 (2H , d, J = 8.5 Hz), 7.43 (2H, d, J = 8.5 Hz), 7.51 (2H, d, J = 8.5 Hz) ppm

Subsequently, compound (I) was obtained by the following scheme.

Specifically, first, 2.00 g (3.65 mmol) of compound (G), 2.88 g (11.8 mmol) of 1,6-dibromohexane, 0.65 g (4.72 mmol) of potassium carbonate, and 3-pentanone 50 mL was placed in a 200 mL eggplant flask and refluxed at 110 ° C. for 6 hours. Meanwhile, the progress of the reaction was confirmed every hour by high performance liquid chromatography (HPLC). After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase and allowed to stand for 30 minutes, followed by pleated filtration. The filtrate was concentrated with an evaporator, acetone was added to the residue, and insolubles were removed by suction filtration. The filtrate was concentrated to obtain 1.50 g (2.11 mmol) of compound (I). The obtained compound (I) was a gray solid, its melting point was 97 to 101 ° C., and the yield was 58%. In addition, Compound (I) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1235-1140 (CF), 640-520 (C-Br) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.52 (4H, quin, J = 4.88 Hz), 1.82 (2H, quin, J = 6.87 Hz), 1.91 (2H, quin, J = 6.87 Hz), 2.28- 2.38 (2H, m), 3.12-3.15 (2H, m), 4.01 (2H, t, J = 6.41 Hz), 6.97 (2H, d, J = 8.55 Hz), 7.41 (2H, d, J = 8.55 Hz) ), 7.50 (2H, dd, J = 8.55, 7.32 Hz) ppm

And the compound (7) was obtained with the following scheme.

Specifically, first, Compound (I) 0.60 g (0.85 mmol), 4-cyano-4′-hydroxybiphenyl 0.17 g (0.85 mmol), potassium carbonate 0.21 g (1.52 mmol), and 50 mL of 3-pentanone was placed in a 200 mL eggplant flask and refluxed at 110 ° C. for 1 day. After completion of the reaction, the mixture was allowed to stand at room temperature and transferred to a separatory funnel. Water, cyclopentyl methyl ether and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 0.40 g (0.48 mmol) of Compound (7). The compound (7) obtained was a white powder, its melting point was 162 to 163 ° C., and the yield was 57%. In addition, compound (7) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 2230 (C≡N), 1235-1240 (CF) cm ^−1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.57 (6H), 1.86 (4H), 2.43 (2H), 3.14 (2H), 4.03 (4H), 6.98 (4H), 7.42 (2H), 7.68 (2H ) ppm

(Example 12)
(Synthesis of Compound (8))
Compound (8) was obtained by the following scheme.

Specifically, first, 0.52 g (0.73 mmol) of compound (I), 0.14 g (0.73 mmol) of 4-fluoro-4′-hydroxybiphenyl, 0.18 g (1.30 mmol) of potassium carbonate, and 50 mL of 3-pentanone was placed in a 200 mL eggplant flask and refluxed at 110 ° C. for 1 day. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Water, ethyl acetate and brine were added thereto to separate into an aqueous phase and an organic phase. Next, anhydrous magnesium sulfate was added to the organic phase, and the mixture was allowed to stand for 30 minutes, then fold-fold filtration was performed, and the filtrate was concentrated with an evaporator to obtain a solid. The obtained solid was purified by silica gel column chromatography with chloroform to obtain 0.06 g (0.07 mmol) of Compound (8). The compound (8) obtained was colorless crystals, the melting point was 181 to 182 ° C., and the yield was 10%. In addition, Compound (8) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.78 (6H), 1.86 (2H), 2.42 (2H), 3.14 (2H), 4.02 (4H), 6.97 (2H), 7.09 (2H), 7.40-7.54 (4H, m) ppm

(Example 13)
(Synthesis of Compound (9))
First, compound (J) was obtained according to the following scheme.

Specifically, first, 0.6 g (0.84 mmol) of Compound (I), 0.21 g (2.1 mmol) of 35 mass% hydrogen peroxide water, and 50 mL of acetic acid were placed in a 200 mL eggplant flask, and 110 ° C. Reflux was performed overnight. After completion of the reaction, the mixture was allowed to stand to room temperature, and 40 mL of 6% by mass sodium bisulfite was added thereto, followed by suction filtration to obtain 0.54 g (0.74 mmol) of compound (J). The compound (J) obtained was colorless crystals, the melting point was 151 to 152 ° C., and the yield was 87%. The compound (J) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1235-1140 (CF), 640-520 (C-Br) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.53 (2H, quin, J = 3.51 Hz), 1.84 (2H, quin, J = 6.71 Hz), 1.92 (2H, quin, J = 7.02 Hz), 2.58- 2.68 (2H, m), 3.36 (2H, tt, J = 8.5, 4.0 Hz), 3.44 (2H, t, J = 6.71 Hz), 4.03 (2H, t, J = 6.41 Hz), 7.00 (2H, d , J = 9.16 Hz), 7.56 (2H, d, J = 9.16 Hz), 7.77 (2H, d, J = 8.55 Hz), 7.96 (2H, d, J = 8.55 Hz) ppm

And the compound (9) was obtained with the following scheme.

Specifically, first, compound (J) 0.52 g (3.89 mmol), 4-fluoro-4′-hydroxybiphenyl 0.13 g, (0.71 mmol), potassium carbonate 0.15 g (1.10 mmol), In addition, 70 mL of cyclohexanone was placed in a 200 mL eggplant flask and refluxed at 160 ° C. for 1 day. After completion of the reaction, the mixture was allowed to stand until it reached room temperature and transferred to a separatory funnel. Thereto, 100 mL of water was added and suction filtration was performed to separate it into a solid and a liquid. The obtained solid was washed with ethyl acetate to obtain 0.03 g (0.04 mmol) of Compound (9). The compound (9) obtained was colorless crystals, the melting point was 190 to 191 ° C., and the yield was 6.0%. In addition, Compound (9) was identified by an infrared spectrophotometer and a nuclear magnetic resonance apparatus. The results are shown below.
IR (KBr): ν = 1235-1140 (CF) cm ^-1
1 H NMR (500 MHz, CDCl ₃ ): δ = 1.58 (6H), 1.86 (2H), 2.61 (2H), 3.36 (2H), 4.05 (4H), 6.97 (2H), 7.09 (2H), 7.77 (2H ), 7.95 (2H) ppm

(Evaluation of gelation ability)
The respective compounds and the organic solvent were mixed while heating in a container to obtain a uniform mixed solution, and then cooled to 25 ° C. to obtain a sample solution. The heating was performed until the compound was dissolved. The container was allowed to stand for 30 minutes in an environment at 25 ° C., and then the container was turned upside down with the sample solution contained therein, and the fluidity at that time was confirmed, and the fluid that lost fluidity was gelled. The gel composition was evaluated as “G”. In addition, the minimum concentration of the compound (concentration of the compound based on the total amount of the gel-like composition) required to change the mixing ratio of the organic solvent and each of the above-mentioned compounds into a gel-like composition is determined on a mass basis ( Mass%). It can be said that the smaller the amount of the compound, the higher the gelation ability. The results are shown in parentheses in Table 1.
On the other hand, when the concentration of each compound in the above sample solution was increased to 5% by mass, it did not gel even when heated, and “S” represents a sol form after standing for 30 minutes in an environment of 25 ° C. The case where the precipitate was formed was evaluated as “P”, and the case where the compound was not dissolved was evaluated as “I”. The results are also shown in Table 1.

Moreover, the result of the _sol-gel transition temperature ( _Tsol-gel ) for every density | concentration (Conc.) Of a compound about the gelatinized sample liquid is shown to FIGS. In the figure, as an organic solvent, “PC” is propylene carbonate, “GBL” is γ-butyrolactone, and “BMIM-TFSA” is ionic liquid 1-butyl-3-methylimidazolium bis (trifluoromethanesulfonyl). Amide, “EMIM-TFSA” is ionic liquid 1-ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) amide, “TMPA-TFSA” is ionic liquid N, N, N-trimethyl-N— Propyl ammonium bis (trifluoromethanesulfonyl) amide, “DEME-TFSA” represents N, N-diethyl-N-methyl-N- (2-methoxyethyl) ammonium bis (trifluoromethanesulfonyl) amide, which is an ionic liquid. .
In addition, the used organic solvent is as showing in Table 1 and FIGS.

(Measurement of phase transition temperature)
For each of the above compounds, the phase transition temperature (ie, melting point) between the crystal and the smectic A phase, the phase transition temperature between the smectic A phase and the isotropic liquid, and between the smectic A phase and the isotropic liquid. The phase change latent heat of was measured as follows.
The phase transition temperature and the latent heat of phase transition were measured using a differential scanning calorimeter (manufactured by Seiko Instruments Inc., product name “SSC-5200DSC”) at a heating rate of 5 ° C. or 10 ° C. per minute. Identification of the liquid crystal phase was performed with a polarizing microscope (manufactured by Nikon Corporation, product name “OHOPTIPHOT2-POL”, optical magnification of 100 times) equipped with a temperature controller (manufactured by Mettler, FP82HT hot stage and FP90 control processor).

  The results are shown in Table 2. In Table 2, “mp” indicates the phase transition temperature between the crystal and the smectic A phase, that is, the melting point, and “SmA-Iso” indicates the phase between the smectic A phase and the isotropic liquid (Iso). A phase transition indicating a transition temperature and a temperature in parentheses (()) indicates a univariate phase transition. ΔH [SmA-Iso] represents the latent heat of phase transition between the smectic A phase and the isotropic liquid. Further, a binary mixture of the compound (1-4) and a compound represented by the following formula (8OCB) (hereinafter referred to as “compound (8OCB)”), a compound (1-6) and a compound (1 -12) and the binary transition mixture of compound (4-6) and compound (8OCB), the phase transition temperature when the composition ratio of each component is changed is the same as above. Measured. The results are shown in FIGS. 15, 16 and 17, “C” indicates a crystal, “SmA” indicates a smectic A phase, “Iso” indicates an isotropic liquid, and “N” indicates a nematic phase. The compound (8OCB) had a phase transition temperature of 55 ° C. between the crystal and smectic A phase, 67 ° C. between the smectic A phase and the nematic phase, and 80 ° C. between the nematic phase and the isotropic liquid.

(Polarized light micrograph)
Compounds (3-4) and (3-6), and two-component system of compound (1-4) and compound (8OCB) (compound (1-4): compound (8OCB)) = 40:60 (molar ratio) )) Polarized micrographs were taken of the mixture. First, a sample compound or a binary mixture was sandwiched between a slide glass and a cover glass, and then heated until the crystals melted and became an isotropic liquid, and cooled to room temperature. The sample crystallized in this way was heated at a temperature of 5 ° C. per minute under a polarizing microscope. After the sample became an isotropic liquid, it was cooled so that the temperature dropped at 5 ° C. per minute.

  With respect to compound (3-4), the crystal melted at 95 ° C. during sample heating and became an isotropic liquid. When the isotropic liquid was cooled, a fan structure characteristic of the smectic A phase was observed at 88 ° C. Further cooling and when the temperature reached 85 ° C., a polarizing micrograph (100 ×) of the fan structure was taken. The photograph is shown in FIG.

  For compound (3-6), the crystal melted at 70 ° C. during sample heating to form a smectic A phase, and when heated, it became an isotropic liquid at 78 ° C. When the isotropic liquid was cooled, a fan structure characteristic of the smectic A phase was observed at 78 ° C. Further cooling was performed, and when the temperature reached 75 ° C., a polarizing micrograph (100 times) of the fan structure was taken. The photograph is shown in FIG.

  For the binary mixture of compound (1-4) and 8OCB, the crystal melts at 92 ° C. during sample heating to form a smectic A phase, and when heated further becomes an isotropic liquid at 100 ° C. It was. During cooling of the isotropic liquid, a fan structure characteristic of the smectic A phase was observed at 100 ° C. Further cooling was performed, and when the temperature reached 95 ° C., a polarizing micrograph (100 times) of the fan structure was taken. The photograph is shown in FIG.

  The novel fluoroalkane derivative of the present invention has gelling ability or exhibits liquid crystallinity. Therefore, the present invention has industrial applicability in the fields of gelling agents and gel compositions containing the same, and liquid crystal compounds and liquid crystal compositions containing the same.

Claims (7)

A fluoroalkane derivative represented by the following general formula (1).
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
(In the formula, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic group having 6 to 30 nuclear atoms, and R ¹ has an oxygen atom or a sulfur atom in the chain. And a saturated or unsaturated divalent hydrocarbon group having 1 to 20 carbon atoms, R represents a group represented by the following general formula (2), and X represents —S— or —SO ₂ —. Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom.
C _m F _{2m + 1} C _p H _2p − (2)
(In the formula, m represents a natural number of 2 to 16, and p represents an integer of 0 to 6. ) A fluoroalkane derivative represented by the following general formula (1).
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
(In the formula, Ar ¹ and Ar ² are each independently a condensed ring having one or more aromatic hydrocarbon rings, or a group in which a plurality of aromatic rings are bonded by a single bond, 1 or more of them represents a group which is an aromatic hydrocarbon ring, and R ¹ is a saturated or unsaturated divalent hydrocarbon having 1 to 20 carbon atoms which may have an oxygen atom or a sulfur atom in the chain. R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms having a perfluoroalkyl group, X represents a group represented by —S— or —SO ₂ —, Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom.) The fluoroalkane derivative according to claim 2, wherein R is a group represented by the following general formula (2).
C _m F _{2m + 1} C _p H _2p -(2)
(In the formula, m represents a natural number of 2 to 16, and p represents an integer of 0 to 6.) The fluoroalkane derivative according to any one of claims 1 to 3, wherein Ar ¹ and Ar ² are each independently a phenylene group or a biphenylene group. A gelling agent comprising a fluoroalkane derivative represented by the following general formula (1) .
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
(In the formula, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic group having 6 to 30 nuclear atoms, and R ¹ has an oxygen atom or a sulfur atom in the chain. A saturated or unsaturated divalent hydrocarbon group having 1 to 20 carbon atoms which may be substituted, and R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms having a perfluoroalkyl group; X represents a group represented by —S— or —SO ₂ —, and Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom. ) A liquid crystalline compound comprising a fluoroalkane derivative represented by the following general formula (1) .
R—X—Ar ¹ —O—R ¹ —O—Ar ² —Y (1)
(In the formula, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted divalent aromatic group having 6 to 30 nuclear atoms, and R ¹ has an oxygen atom or a sulfur atom in the chain. A saturated or unsaturated divalent hydrocarbon group having 1 to 20 carbon atoms which may be substituted, and R represents a saturated or unsaturated monovalent hydrocarbon group having 2 to 22 carbon atoms having a perfluoroalkyl group; X represents a group represented by —S— or —SO ₂ —, and Y represents a cyano group, a nitro group, a saturated or unsaturated monovalent alkoxyl group having 2 to 20 carbon atoms, or a fluorine atom. )   A gel composition containing the gelling agent according to claim 5 and an organic solvent.