JP2002241734A - Self-assembly monomolecular film and method for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prepare a self assembly monomolecular film capable of preventing reduction of a free space caused by aggregation of self assembly compounds themselves, thus, ensuring a free space in which an azobenzene unit can be isomerized and surface characteristics can be effectively and uniformly changed. SOLUTION: The self assembly monomolecular film is characterized in that the film is formed by adhering an azobenzene derivative represented by formula (1) (wherein R1 represents a 3-21C alkylene; X represents at least one kind selected from the group consisting of OH, a straight or branched chain 1-22C alkyl, a straight or branched chain 1-22C oxyalkyl, a straight or branched chain 1-22C fluorinated alkyl, a 1-21C alcoholic residue, a 1-21C aliphatic carboxylic acid residue and an aryl which may have a substituent) onto a base material. The method for producing the same is also provided.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a self-assembled monolayer containing an azobenzene derivative.

[0002]

2. Description of the Related Art When a so-called self-assembling compound is adsorbed (chemically adsorbed) on a specific substrate surface, its molecular assembling property (adsorption action by an adsorbing functional group and a group bonded to the adsorbing functional group) ), The self-assembling compounds are arranged almost regularly on the surface of the base material. A film formed by such an arrangement is used as a self-assembled monolayer or a self-assembled monolayer (Self-Assembled).
Monolayers, abbreviated as SAM). Since the surface of the self-assembled monolayer has the terminal groups of the molecules of the self-assembled compound molecules densely arranged, the physical properties of the terminal groups affect the surface characteristics of the self-assembled monolayer, for example, the self-assembled compound. It is known that the wettability of the surface of the self-assembled monolayer changes greatly depending on the presence or absence of adsorption (Colind. Bain, E. Varry Troughton, Yu-Tai Tao, Jo
seph Evall, George M. Whitesides, and Ralph G. Nuzzo
, J. Am. Chem. Soc., 111, 321-335 (1989)). on the other hand,
Although a method of changing the molecular structure of the self-assembling compound molecule to change its surface characteristics is also conceivable, as described above, since the conventional self-assembled monolayer has a very dense structure, the surface characteristics are changed. However, there is no free space required for the change in the self-assembled monolayer, and it is difficult to change the molecular structure. For example, azobenzene (known as a photochromic material having a property of being photoisomerized from a trans form to a cis form by absorbing ultraviolet light and returning to the trans form by irradiating visible light or heating to the cis form). In the case of a self-assembled monolayer having a long-chain alkanethiol having a self-assembling compound,
It has been confirmed that free space required for isomerization of azo groups does not exist due to the very dense membrane structure (R. Wang, T. Iyod
a, L. Jiang, DATryk, K. Hashimoto, A. Fujishima
, J. Electroanal. Chem., 438, 213-219 (1997)). To overcome such disadvantages, Japanese Patent Application Laid-Open No. 2000-264
No. 874 discloses that a long-chain alkanethiol having azobenzene and a self-assembling compound obtained by disulfide-forming an alkanethiol having a relatively short chain length are synthesized, and a self-assembled monomolecular film is formed using the compound. Inventions that have achieved isomerization are described.

[0003] However, Japanese Patent Laid-Open No. 2000-26487.
The substance used in the invention described in Japanese Patent Publication No. 4 (2004) is a substance in which chains having different properties are linked by disulfide formation, so that micro-layer separation is apt to occur during the formation of a self-assembled monolayer, and the azo unit However, there is a problem that the free space between the self-assembling compounds is reduced, and the azo unit is unlikely to exhibit the original isomerization ability.

[0004]

SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned problems of the prior art, and prevents a reduction in free space due to agglomeration of self-assembling compounds. It is an object of the present invention to provide a self-assembled monolayer in which a free space that can be converted is secured and the surface characteristics can be changed efficiently and uniformly.

[0005]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to achieve the above object, and as a result, have found that an ester group is present in the molecule of a long-chain alkanethiol having an azobenzene group constituting a self-assembled monolayer. It has been found that the use of a self-assembling compound having an isomer allows the azo unit to be efficiently isomerized and the surface characteristics to be reliably changed, thereby completing the present invention.

That is, the self-assembled monolayer of the present invention comprises:
General formula (1)

[0007]

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[In the formula (1), R ¹ represents an alkylene group having 3 to 21 carbon atoms, X represents a hydroxyl group, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched alkyl group, A branched oxyalkyl group having 1 to 22 carbon atoms, a linear or branched fluorinated alkyl group having 1 to 22 carbon atoms, an alcohol residue having 1 to 21 carbon atoms, and 1 to 21 carbon atoms At least one selected from the group consisting of an aliphatic carboxylic acid residue and an aryl group which may have a substituent. ]
A self-assembled monomolecular film characterized by being formed by adsorbing an azobenzene derivative represented by the formula on a substrate.

The method for producing a self-assembled monolayer according to the present invention is represented by the general formula (1):

[0010]

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[In the formula (1), R ¹ represents an alkylene group having 3 to 21 carbon atoms; X represents a hydroxyl group, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched alkyl group; A branched oxyalkyl group having 1 to 22 carbon atoms, a linear or branched fluorinated alkyl group having 1 to 22 carbon atoms, an alcohol residue having 1 to 21 carbon atoms, and 1 to 21 carbon atoms At least one selected from the group consisting of an aliphatic carboxylic acid residue and an aryl group which may have a substituent. ]
A method for producing a self-assembled monomolecular film, comprising a step of adsorbing an azobenzene derivative represented by formula (1) on a substrate.

[0012]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Preferred embodiments of the present invention will be described below in detail.

The self-assembled monolayer of the present invention has the general formula (1)

[0014]

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In the formula (1), R ¹ represents an alkylene group having 3 to 21 carbon atoms, X represents a hydroxyl group, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched alkyl group, A branched oxyalkyl group having 1 to 22 carbon atoms, a linear or branched fluorinated alkyl group having 1 to 22 carbon atoms, an alcohol residue having 1 to 21 carbon atoms, and 1 to 21 carbon atoms At least one selected from the group consisting of an aliphatic carboxylic acid residue and an aryl group which may have a substituent. ]
Is a self-assembled monomolecular film characterized by being formed by adsorbing an azobenzene derivative represented by the formula on a substrate.

First, the compound of the general formula (1) according to the present invention will be described.

The compound of the general formula (1) according to the present invention is
It has a structure in which an alkanethiol group is bonded to an azobenzene group having X as a side chain via an ester bond.

X is a hydroxyl group, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched oxyalkyl group having 1 to 22 carbon atoms, a linear or branched oxyalkyl group, A branched fluorinated alkyl group having 1 to 22 carbon atoms, an alcohol residue having 1 to 21 carbon atoms, an aliphatic carboxylic acid residue having 1 to 21 carbon atoms, and an aryl group which may have a substituent At least one selected from the group consisting of

The alkyl group according to the present invention is a linear or branched alkyl group having 1 to 22 carbon atoms, preferably an alkyl group having 5 to 15 carbon atoms. Examples of such an alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, an isopentyl group, and a hexyl group. Can be

The oxyalkyl group according to the present invention is a linear or branched alkyl group having 1 to 22 carbon atoms, preferably an alkyl group having 5 to 15 carbon atoms. Examples of such an oxyalkyl group include a methoxy group, an ethoxy group, a propoxy group,
t-butoxy group, pentoxy group, isopentoxy group,
A hexoxy group and a heptoxy group are exemplified.

The fluorinated alkyl group according to the present invention is a linear or branched fluorinated alkyl group having 1 to 22 carbon atoms, and particularly a fluorinated alkyl group having 1 to 10 carbon atoms. Preferably, there is. Examples of such a fluorinated alkyl group include a 3,3,3-trifluoropropyl group, a pentafluorobutyl group, a heptafluoropentyl group, a nonafluorohexyl group, a heptadecafluorodecyl group, a tridecafluoroisooctyl group Is mentioned. Here, in the fluorinated alkyl group, it is not necessary that all hydrogen atoms of the alkyl group be substituted with fluorine atoms, and a fluorine atom in which some hydrogen atoms (preferably 20% or more) are substituted with fluorine atoms. Fluorinated alkyl groups are also included in the fluorinated alkyl groups according to the present invention.

The alcohol residue according to the present invention is
It is an alcohol residue having 1 to 21 carbon atoms, and particularly preferably 1 to 10 carbon atoms. Such alcohol residues include, for example, methanol residue, ethanol residue, n-propanol residue, n-butanol residue, s
-Butanol residue, t-butanol residue, n-pentanol residue, n-hexanol residue, n-heptanol residue, n-octanol residue, isohexanol residue.

The aliphatic carboxylic acid residue according to the present invention is an aliphatic carboxylic acid residue having 1 to 21 carbon atoms, and preferably has 1 to 10 carbon atoms. Examples of such an aliphatic carboxylic acid residue include an acetic acid residue, a propionic acid residue, a 2-ethylhexanoic acid residue,
Perfluorooctanoic acid residues, α-hydroxycarboxylic acid residues, glycolic acid residues, lactic acid residues, and mandelic acid residues are exemplified.

Further, examples of the aryl group according to the present invention include a phenyl group, a tolyl group, a xylyl group, a biphenyl group, a naphthyl group, an anthryl group and a phenanthryl group. The aryl group may have a substituent, and examples of such a substituent include a halogen atom, a hydroxyl group, an amino group, an alkyl group, an alkoxy group, and an aryloxy group. It is preferably a group. Such an alkyl group is a linear or branched alkyl group having 1 to 22 carbon atoms (alkyl residue), and specifically includes, for example, a methyl group, an ethyl group, a propyl group, and an isopropyl group. , N-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, isopentyl group and hexyl group.

The terminal group X described above is bonded to an azobenzene group as shown in the general formula (1). Here, the azobenzene group has a structure in which a benzene ring is bonded to both ends of the azo group, and the bonding mode may be either a cis form or a trans form.

The azobenzene group has an alkanethiol group bonded via an ester bond to the other end of the end where X is bonded. The alkylene group (R ¹ ) constituting such an alkanethiol preferably has 3 to 21 carbon atoms, more preferably 5 to 15 carbon atoms. If the number of carbon atoms is less than the lower limit, it tends to be difficult to obtain sufficient uniformity of the self-assembling compound adsorbed on the substrate, and if the number of carbon atoms is more than the upper limit, it tends to take time to form a self-assembled monolayer. is there.

In such an alkanethiol, since the sulfur contained in the terminal thiol group has an affinity for the substrate, the self-assembling compound having the alkanethiol can form a self-assembled monolayer. Becomes

In such a self-assembled monolayer, the space between adjacent self-assembled compounds is sufficiently maintained due to the presence of the ester bond in the self-assembled compound, and the azo unit isomerized. The necessary free space is fully secured.

Next, a method for producing the self-assembled monolayer of the present invention will be described.

The method for producing a self-assembled monomolecular film according to the present invention comprises:
General formula (1)

[0031]

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[In the formula (1), R ¹ represents an alkylene group having 3 to 21 carbon atoms, X represents a hydroxyl group, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched alkyl group, A branched oxyalkyl group having 1 to 22 carbon atoms, a linear or branched fluorinated alkyl group having 1 to 22 carbon atoms, an alcohol residue having 1 to 21 carbon atoms, and 1 to 21 carbon atoms At least one selected from the group consisting of an aliphatic carboxylic acid residue and an aryl group which may have a substituent. ]
Wherein the step of adsorbing the azobenzene derivative represented by

The method for adsorbing the compound represented by the general formula (1) on the substrate is not particularly limited, and the compound may be adsorbed on the substrate using a known method. Specifically, for example, the above-described base material is generally immersed in a solution in which the compound represented by the general formula (1) is dissolved, and then taken out. A substrate on which the compound represented by the formula (1) is adsorbed can be obtained. Examples of the solvent for dissolving the compound represented by the general formula (1) include methanol, a mixed solution of methanol and water, ethanol, THF, diethyl ether, and dichloromethane. Preferably, it is used. Further, examples of the washing liquid include methanol, a mixed solution of methanol and water, ethanol, THF, diethyl ether, and dichloromethane. Among them, a mixed solution of methanol and water and ethanol are preferable. Here, the immersion conditions include, for example, a concentration of the solvent of 0.1 to 1
0 mmol, more preferably 1-2 mmol, and the temperature condition is 0-60 ° C.
(Below the boiling point of the solvent), and is preferably room temperature to 40 ° C.
More preferably, the time is 12 to 48
It is preferably time.

The self-assembled monolayer produced in this manner has the characteristic of a self-assembled monolayer having a very dense film structure on the surface of the substrate, and has an ester in the self-assembled compound. By the presence of the group, the space between adjacent self-assembling compounds is sufficiently maintained. Therefore,
Aggregation between self-assembling compounds is sufficiently prevented, micro-layer separation does not occur in the self-assembled monolayer, and sufficient free space required for isomerization of the azo unit is secured.

The method for isomerizing azo units in the self-assembled monolayer of the present invention to change the surface characteristics of the self-assembled monolayer is described below.

The isomerization of the azo unit can be carried out, for example, by using any one of the methods of irradiation with ultraviolet light, irradiation with visible light and heating alone. It is possible to more effectively perform isomerization by appropriately combining

As the irradiation conditions of such ultraviolet light, the wavelength range of the ultraviolet light is preferably 300 to 400 nm, whereby the azo unit tends to isomerize from the trans form to the cis form. When the range of the ultraviolet light is smaller than the lower limit, ozone is generated and the self-assembled monolayer tends to be easily decomposed.

The visible light irradiation conditions are preferably such that the wavelength range of visible light is 400 to 800 nm, and more preferably 400 to 500 nm.
The azo unit tends to isomerize from the cis-form to the trans-form by irradiation with visible light.

The heating conditions are 50 to 1
It is preferable to heat at 50 ° C., and the heating time is 1 to 10
Minutes. The azo unit tends to isomerize from the cis form to the trans form by heating.

Thus, the surface properties of the self-assembled monolayer of the present invention can be reversibly changed by the isomerization of the azo unit. It is possible to change surface properties such as adhesion.

[0041]

EXAMPLES The present invention will now be described more specifically with reference to examples, but the present invention is not limited to the following examples.

Example 1 <Step 1> 250 ml of an aqueous solution of about 0.19 N hydrochloric acid was added to 6.2 mmol of 4-pentylaniline, and the mixture was stirred at room temperature for 30 minutes. After cooling this solution to 0-5 ° C,
9.3 mmol of sodium nitrite were added and an additional 30
After stirring for minutes, a white precipitate formed. Add about 0.2 to this solution
6.2 mm in 100 ml of 5N sodium hydroxide aqueous solution
ol of a phenol solution was added with stirring at room temperature, then cooled to 0 to 5 ° C., and stirred for 3 hours. After the obtained solution was returned to room temperature, dilute hydrochloric acid was added until the pH of the solution became about 3, and a loess-colored precipitate was formed. The resulting precipitate is filtered off with suction and dried under reduced pressure to give the intermediate (I)
I got The synthetic route of the intermediate (I) is shown below.

[0043]

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The results of NMR of the intermediate (I) are shown below. ¹ H NMR (60 MHz: CDCl ₃ ) δ (ppm): 0.81-0.99 (t, 3H, -C
H ₃ ), 1.32-1.78 (m, 6H, -C H ₂ C H ₂ C H _2- ) 2.57-2.81 (t, 2H, A
_{r-CH 2 -), 7.73-8.08} (m, -Ar H), 7.39-7.93 (m, -Ar H).

<Step 2> In 5 ml of dry dichloromethane, 0.26 mmol of 11-mercaptoundecanoic acid, 0.29 mmol of intermediate (I), 0.21 mmol
l of 4- (dimethylamino) pyridine was added, and the mixture was stirred well while maintaining at 0 ° C. While maintaining this solution at 0 ° C., 0.31 mmol of 1,3-dicyclohexylcarbodiimide (hereinafter, DC) is added to 2 ml of dry dichloromethane.
C) was slowly added dropwise. The solution was stirred at 0 ° C. for a further 20 minutes before returning to room temperature,
After stirring for 24 hours, a precipitate was formed. The resulting precipitate was collected by filtration, the filtrate was collected in a separating funnel, and concentrated citric acid several times.
The mixture was washed thoroughly with several portions of saturated sodium bicarbonate by shaking. After a small amount of magnesium sulfate was added to the filtrate and dried overnight, the supernatant was dried under reduced pressure to obtain a crude product.
This was dissolved in dry hexane, suction filtered, and the filtrate was dried under reduced pressure to obtain a compound. The route of the synthesis and the compounds obtained are shown below.

[0046]

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The results of NMR of the compound are shown below. ¹ H NMR (60 MHz: DMSO-d ₆ ) δ (ppm): 0.94-1.52 (m),
2.47−2.70 (m, -SC H _2- , Ar-C H ₂ , -C H ₂ -COO-), 7.15-7.38
(m, Ar H), 7.77-8.01 (m, -Ar H).

Example 2 In place of Intermediate (I), 4- (4-decyloxyphenylazo) phenol (manufactured by SIGMA-ALDRICH)
, And the subsequent steps are described in Example 1 <Step 2
The synthesis of an azobenzene derivative was carried out in the same manner as in>. The synthetic route and the obtained compound are shown below.

[0049]

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The results of NMR of the obtained compound are shown below. ¹ H NMR (60 MHz: DMSO-d ₆ ) δ (ppm): 0.99-1.52 (m),
2.48−2.60 (m, 4H, -SC H ₂ -,-C H ₂ -COO-), 3.96-4.32 (m, 2
H, Ar-OC H _2- ), 6.93-7.27 (m, -Ar H ), 7.85-8.74 (m, -Ar
H ).

Example 3 <Step 1> 250 ml of an aqueous solution of about 0.19 N hydrochloric acid was added to 6.2 mmol of 4-pentylaniline, and the mixture was stirred at room temperature for 30 minutes. After cooling this solution to 0-5 ° C,
9.3 mmol of sodium nitrite were added and an additional 30
After stirring for minutes, a white precipitate formed. Add about 0.2 to this solution
6.2 mm in 100 ml of 5N sodium hydroxide aqueous solution
ol of a phenol solution was added with stirring at room temperature, then cooled to 0 to 5 ° C., and stirred for 3 hours. After the obtained solution was returned to room temperature, dilute hydrochloric acid was added until the pH of the solution became about 3, and a loess-colored precipitate was formed. The resulting precipitate is filtered off with suction and dried under reduced pressure to give the intermediate (I)
I got

The results of NMR of the intermediate (I) are shown below. ¹ H NMR (60 MHz: CDCl ₃ ) δ (ppm): 0.81-0.99 (t, 3H, -C
H ₃ ), 1.32-1.78 (m, 6H, -C H ₂ C H ₂ C H _2- ) 2.57-2.81 (t, 2H, A
_{r-CH 2 -), 7.73-8.08} (m, -Ar H), 7.39-7.93 (m, -Ar H).

[0053]

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<Step 2> In 5 ml of ethanol:
56 mmol of 15-bromopentadecanoic acid and 2.3 m
mol of thiourea was added and the mixture was heated and refluxed at 70 ° C. for 16 hours. A solution obtained by dissolving 2.9 mmol of sodium hydroxide in 5 ml of distilled water was added to the above solution, and the mixture was further refluxed for 3 hours and then cooled to room temperature. When the pH of the solution was adjusted to about 3 by adding dilute hydrochloric acid to the solution, a white precipitate (crude product) was deposited. This was filtered by suction, dried under reduced pressure, dissolved in chloroform, filtered by suction, and the filtrate was concentrated. The concentrated solution was dried under reduced pressure to obtain 14-carboxy-1-pentadecanethiol (intermediate (II)). The intermediate (I)
1 shows a synthetic scheme of I).

[0055]

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The results of NMR of the intermediate (II) are shown below. ¹ H NMR (60 MHz: CDCl ₃ ) δ (ppm): 1.27-1.63 (m, 28H,-
(C H ₂ -,-SH) 2.24-2.81 (m, 6H, -S-CH ₂ , -CH ₂ -COO-) <Step 3> 0.37 in 5 ml of dry dichloromethane
mmol of 14-carboxy-1-pentadecanethiol (intermediate (II)), 0.40 mmol of intermediate (I) and 0.29 mmol of 4- (dimethylamino) pyridine are added, and the mixture is kept well at 0 ° C. Stirred. Add 0.4 ml of this solution to 2 ml of dry dichloromethane.
A solution in which 4 mmol of 1,3-dicyclohexylcarbodiimide was dissolved was slowly added dropwise (the temperature of the solution was 0%).
C.). After stirring at 0 ° C. for another 20 minutes, the temperature was returned to room temperature, and the mixture was stirred for 24 hours to produce a precipitate. The resulting precipitate was collected by filtration, and the filtrate was taken into a separating funnel and washed with concentrated citric acid several times and with saturated sodium bicarbonate by shaking well. After a small amount of magnesium sulfate was added to the filtrate and dried overnight, the supernatant was taken out and dried under reduced pressure to obtain a crude product. This was dissolved in dry hexane, suction filtered, and the filtrate was dried under reduced pressure to obtain a compound. The synthetic route of the compound and the compound are shown below.

[0057]

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The results of NMR of the compound are shown below. ¹ H NMR (60 MHz: DMSO-d ₆ ) δ (ppm): 0.82-1.78 (m),
2.35-2.80 (m, 6H, -SC H _2- , Ar-C H ₂ -,-C H ₂ -COO-), 7.07-7.
38 (m, -Ar H), 7.77-8.30 (m, -Ar H).

Example 4 ( Preparation of Self-Assembled Monolayer and Confirmation of Photoisomerization) After depositing 5 nm of chromium on a washed glass substrate, 200 n
m of gold was deposited. This substrate was added to a 1 mM ethanol solution of the azobenzene derivative prepared in Examples 1 to 3 for 48 hours.
After soaking for more than an hour, it was taken out of the solution, the surface was rinsed with ethanol, and excess thiol was washed away to prepare a SAM-modified surface having an azobenzene derivative chemically adsorbed on the surface.

Using this SAM-modified surface, the photoisomerization of the azobenzene derivative was confirmed by the following method by changing the contact angle. For light irradiation, a 200 W mercury-xenon lamp was used as a light source, and at the time of ultraviolet light irradiation, a visible light absorbing filter was attached thereto, and only ultraviolet light was irradiated. At the time of visible light irradiation, an ultraviolet light absorbing filter was attached, and only visible light was irradiated. Irradiation of visible light with the contact angle of the sample surface to water (4
(800-800 nm), UV light irradiation (300-400n)
m) The measurement was performed after visible light irradiation (400 to 800 nm), and the change was observed.

As is clear from the results shown in FIG. 1, the contact angles are changed by the processes of visible light irradiation, ultraviolet light irradiation, and visible light irradiation. This indicates that azobenzene isomerized into cis form by ultraviolet light and isomerized again into trans form by visible light.

Comparative Example 1 A change in the contact angle of a self-assembled monolayer was examined in the same manner as in Example 4 using the compound shown as the compound as a self-assembled compound. The structure of the compound is shown below.

[0063]

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As is evident from the results shown in FIG. 2, no change in the contact angle was observed by treatment with visible light irradiation, ultraviolet light irradiation, and visible light irradiation. This indicates that azobenzene is not isomerized. It is considered that the reason why azobenzene was not isomerized was that there was not enough space for azobenzene isomerization because the compounds were very densely assembled in the self-assembled monolayer.

[0065]

As described above, according to the self-assembled monolayer of the present invention, the free space is prevented from decreasing due to the aggregation of the self-assembling compounds, and as a result, the free space in which the azobenzene unit can be isomerized is prevented. It is possible to provide a self-assembled monolayer capable of efficiently and uniformly changing the surface characteristics.

[Brief description of the drawings]

FIG. 1 is a graph showing the relationship between the isomerization of a self-assembled compound represented by the chemical formula (1) and the change in the contact angle of a self-assembled monolayer.

FIG. 2 is a graph showing a relationship between isomerization of a self-assembled compound represented by a chemical formula and a change in contact angle of a self-assembled monolayer.

 ──────────────────────────────────────────────────続 き Continued on the front page F-term (reference) 4H006 AA03 TA04 4H020 BA21

Claims (2)

[Claims] 1. A compound of the general formula (1) [In the formula (1), R ¹ represents an alkylene group having 3 to 21 carbon atoms, X represents a hydroxyl group, a linear or branched carbon atom having 1 carbon atom.
Alkyl group having 1 to 22 carbon atoms, linear or branched oxyalkyl group having 1 to 22 carbon atoms, linear or branched fluorinated alkyl group having 1 to 22 carbon atoms, 1 to 21 carbon atoms
At least one selected from the group consisting of an alcohol residue, an aliphatic carboxylic acid residue having 1 to 21 carbon atoms, and an aryl group which may have a substituent. ] The self-assembled monomolecular film characterized by being formed by adsorbing the azobenzene derivative represented by the formula (1) on a substrate. 2. A compound of the general formula (1) [In the formula (1), R ¹ represents an alkylene group having 3 to 21 carbon atoms, X represents a hydroxyl group, a linear or branched carbon atom having 1 carbon atom.
Alkyl group having 1 to 22 carbon atoms, linear or branched oxyalkyl group having 1 to 22 carbon atoms, linear or branched fluorinated alkyl group having 1 to 22 carbon atoms, 1 to 21 carbon atoms
At least one selected from the group consisting of an alcohol residue, an aliphatic carboxylic acid residue having 1 to 21 carbon atoms, and an aryl group which may have a substituent. ] A method for producing a self-assembled monomolecular film, comprising a step of adsorbing the azobenzene derivative represented by the formula (1) on a substrate.