JPH02256692A - New ferrocene derivative, surfactant containing same derivative and production of organic thin film - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I [Y is -O- or-C(O)O-; n is 6-13; m is 5.0-30.0]. EXAMPLE:A compound expressed by formula II. USE:A surfactant. PREPARATION:Dimethyl ferrocene expressed by formula III is reacted with a dicarboxylic acid derivative expressed by formula IV in a solvent such as methylene chloride in the presence of a Friedel Craft catalyst to afford a compound expressed by formula V, which is then reacted with an alkali such as potassium hydroxide in a solvent such as methanol at 0-150 deg.C to carry out hydrolysis of ester. Then the product is subjected to Clemmensen reduction using zinc, etc., and concentrated hydrochloric acid as a reducing agent in an alcohol solvent at 0-150 deg.C to give a compound expressed by formula IV (R is alkyl of alcohol used to the solvent), which is then reacted with a polyethylene glycol expressed by the formula HO(CH2CH2O)mH in the presence of an acid catalyst at 0-200 deg.C.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel ferrocene derivative, a surfactant containing the same, and a method for producing an organic thin film. 1 each group
A new ferrocene derivative with a structure in which a long chain substituent containing a polyoxyethylene chain is bonded to one of the five-membered rings, and a new ferrocene derivative containing the ferrocene derivative and capable of solubilizing hydrophobic organic substances such as phthalocyanine. The present invention relates to a surfactant that can be used as a surfactant, a method for solubilizing a hydrophobic organic substance using this surfactant, and a method for producing a thin film thereof.

[Prior art and problems to be solved by the invention] In general, dyes such as phthalocyanine or its derivatives are insoluble in water, and dimethylformamide (DM
Although it is soluble in organic solvents such as F) and tetrahydrofuran (THF), the amount of solubilization is small, and the solubility is only about a few square centimeters.

Surfactants for dissolving phthalocyanine and other substances in water have been researched for some time, but a satisfactory solution has not yet been developed.For functional group-substituted phthalocyanine derivatives, sulfonic surfactants are used to slightly dissolve water. Although it has been reported that it can be dissolved, the solubility is not necessarily high enough, and moreover, unsubstituted phthalocyanine cannot be dissolved at all.

Furthermore, surfactants are being researched to dissolve water-insoluble polymers in the same way as mentioned above.
The current situation is that sufficient results have not yet been obtained.

The group of the present inventors recently developed a ferrocene derivative having a polyoxyethylene chain as a surfactant for solubilizing pigments such as phthalocyanine and its derivatives, or water-insoluble polymers. We have developed a method for forming organic thin films using the so-called micelle electrolysis method (International Publication WO89101939).

The present inventors further conducted intensive studies to improve the solubilization ability and electrolytic ability of the above ferrocene derivative. As a result, it was found that ferrocene derivatives having a polyoxyethylene chain and having one methyl group in each of the two five-membered rings of the ferrocene skeleton have an extremely high ability to solubilize hydrophobic organic substances (and also have micellar It has been found that the electrolytic performance during the electrolytic method is good and the film forming rate is high.

The present invention was completed based on this knowledge.

(Means for Solving the Problems) That is, the present invention provides a novel ferrocene derivative represented by - machining allowance is an integer of 6 to 13, and m is a real number of 5.0 to 30.0; A surfactant containing a novel ferrocene derivative is provided.Furthermore, the present invention provides a hydrophobic surfactant characterized in that a hydrophobic organic substance is solubilized in an aqueous medium with a surfactant containing the novel ferrocene derivative. The present invention also provides a method for solubilizing an organic substance, and a method for producing an organic thin film, which comprises electrolyzing a micellar solution obtained by this solubilization method to form a thin film of the hydrophobic organic substance on an electrode.

The ferrocene derivative of the present invention is represented by -a formula (1). It is a ferrocene derivative. The bonding position of the methyl group in the five-membered ring of the ferrocene skeleton is the α position, that is, the one represented by the general formula, and the β position, that is, the one represented by the general formula, with respect to the binding position of the long chain substituent having a polyoxyethylene chain. It can be divided into two types.

The ferrocene derivative of the present invention is one of these two types or a mixture of both.

In the ferrocene derivative of the present invention, Y represents oxygen.

Therefore, -a formula (N is a general formula and - substitute, means not only an integer from 5.0 to 30.0 but also a real number including this, and indicates the average value of the repeating number of these groups) It is.

Such a novel ferrocene derivative represented by the radical (I) can be produced by various methods. Specifically, when Y is an oxycarbonyl group (-C-0-), it can be produced as follows. In other words, in a solvent such as methylene chloride, carbon disulfide, carbon tetrachloride, or ethane dichloride, the length of the carbon chain between the ferrocene ring and the oxygen or oxycarbonyl group, that is, n, is 6. An integer of 13 to 13, particularly preferably an integer of 8 to 11. If n is an integer less than 6, the ability to solubilize a hydrophobic organic substance will be low, and if n is an integer greater than 13, the hydrophilicity of the ferrocene derivative itself will be undesirable.

Further, m represents the number of repeating oxyethylene groups, and dimethylferrocene is represented by the general formula [where n is the same as above]. ] A derivative of a dicarboxylic acid represented by the following formula, in which one side is ethyl esterified and the other side is chloroacylated, is heated with a free-solutafluorocatalyst (eg, AlC1z, FeC1z).

In the presence of FeCl3.5bC1s, 5nC14, etc.), 0
The reaction is carried out at a temperature of .degree. C. to reflux to give -removal amount [wherein n is the same as above. ] A compound represented by is obtained. In this reaction, the positional relationship between the side chain of ferrocene and the methyl group is obtained by mixing both a compound at the α-position represented by the -money and a compound at the β-position represented by the -money.

Here, if it is necessary to separate the compounds represented by [■°] and (IV'l), use a mixed solvent (for example, hegisan: ethyl acetate 5:1) using column chromatography.
etc.).

Next, the compound represented by the -a formula (IV) is reacted with an alkali such as potassium hydroxide or sodium hydroxide in a solvent such as methanol or ethanol at a temperature of 0°C to 150°C to form an ester. is hydrolyzed, and the general formula [where n is the same as above] is carried out. ] A compound represented by is obtained. Subsequently, the compound of -removal allowance (V) is subjected to Talemensen reduction at 0 to 150 °C in an alcohol (methanol, ethanol, etc.) solvent using zinc or zinc amalgam and concentrated hydrochloric acid as a reducing agent, -
[In the formula, n is the same as above, and R is an alkyl group of the alcohol used as the solvent, such as a methyl group or an ethyl group. ] A compound represented by is obtained.

Furthermore, in the presence of a compound of -trium (Vl) and an acid catalyst such as hydrochloric acid, sulfuric acid, P-)luenesulfonic acid, trifluoroacetic acid, etc. . ] Polyethylene glycol represented by
By carrying out the reaction at ~200°C, the general formula [where n
and m are the same as above. ] A compound of the present invention is obtained.

Further, for example, when Y is oxygen (-〇-), it can be produced as follows. That is, a compound represented by -total allowance (It) and the general formula [wherein n is the same as above]. ] The compound represented by the above general formula (II) and (II
The reaction was carried out under the same conditions as the reaction of (l,), and the reaction was carried out under the same conditions as the reaction of -removal [wherein n is the same as above. ] Obtain a compound represented by 0. Next, the compound of -triage [■'] is diluted with tetrahydrofuran; 1° in the presence of a reducing agent such as sodium borohydride (NaBH4) or lithium aluminum hydride (LiAj!H4). By reacting in an aprotic polar solvent such as 4-dioxane, diethyl ether, or dimethyl ether at a temperature ranging from room temperature to reflux temperature, the reaction mixture can be converted to -morimo [where n is the same as above]. ] A compound represented by these is obtained. Then general formula (IX)
Add carbon tetrachloride or carbon tetrabromide to the compound in chloroform solvent in the presence of triphenylphosphine at 0°C to
It is made to react in the reflux temperature range, and is halogenated, -removal [wherein n is the same as above, and X shows a halogen atom. ] A compound represented by the following is produced. In this reaction, when carbon tetrachloride is used as a reaction raw material, it can also be used as a solvent.

The compound of general formula (X) obtained by the above reaction,
-React with a polyethylene glycol compound represented by [■] at O to 200'C in the presence of an alkali metal such as sodium, lithium, potassium, etc., and -React [where n and m are the same as above] . ] The compound of the present invention can be obtained.

The novel ferrocene derivative of the present invention obtained by the method described above is effective as a surfactant, and can particularly be used as a surfactant (micellar agent) for solubilizing hydrophobic organic substances in an aqueous medium. When using the ferrocene derivative of the present invention as a micellizing agent, a compound having a side chain (long chain substituent) having a methyl group and a polyoxyethylene group as described above in the α position [I°] and the β position A mixture of compounds [B] may be used, or only one of the compounds at the α-position or the β-position may be used.

The surfactant of the present invention contains the ferrocene derivative represented by the above-mentioned removal allowance (1) as a main component, and various other additives may be added as appropriate.

By using the surfactant of the present invention, it is possible to solubilize various hydrophobic organic substances in an aqueous medium. There are various types of such hydrophobic organic substances, such as phthalocyanine, metal complexes of phthalocyanine and derivatives thereof, naphthalocyanine, metal complexes of naphthalocyanine and derivatives thereof, porphyrin, metal complexes of porphyrin and these. Including derivatives of optical memory dyes and organic dyes, 1,1゛-dihbutyl-4,4
Electrochromic materials such as °-bipyridinium dibromide, -2,2
Photosensitive materials (photochromink materials) such as ゛-indoline) (commonly known as spiropyran), optical sensor materials, pigments for liquid crystal displays such as p-azoxyanisole, and ``Color Chemical Encyclopedia'' CMC Co., Ltd., March 1988. 2
Pigments for electronics and recording dyes listed on pages 542 to 717 published on the 8th.

Environmental chromism pigments, photographic pigments, energy pigments, biomedical pigments 1 food and cosmetic pigments, dyes,
Examples include hydrophobic compounds of pigments and special coloring dyes. In addition, 7.7,8°8-tetracyanoquinodimethane (TCNQ) and tetrathiafulvalene (TTF)
Organic conductive materials such as 1:1tHt=, gas sensor materials, and photocurable paints such as pentaerythritol diacrylate.

Insulating materials such as stearic acid, 1-phenylazo-2-
Examples include diazo-type photosensitive materials such as naphthol and paints. Furthermore, water-insoluble polymers,
For example, polycarbonate polystyrene, polyethylene,
Polypropylene, polyamide, polyphenylene sulfide (PPS).

General-purpose polymers such as polyphenylene oxide (PPO) and polyacrylonitrile (PAN), as well as polyphenylene, polypyrrole, and polyaniline.

Examples include polythiophene, acetylcellulose, polyvinyl acetate, polyvinyl butyral, and various other polymers (such as polyvinylpyridine) or copolymers (such as copolymers of methyl methacrylate and methacrylic acid).

There are various ways in which the novel ferrocene derivative of the present invention can be used as a surfactant, but it is particularly effective when used as a micelle agent in the method of producing an organic thin film of the present invention. Said - Transfer allowance (1)
Add a surfactant (micelle-forming agent) made of a novel ferrocene derivative (concentration is higher than the micelle concentration limit), a supporting salt, and a hydrophobic organic substance, and thoroughly disperse the mixture using ultrasonic waves, a homogenizer, a stirrer, etc. to form micelles. Form. The heating time is usually 1 hour to 10 days, preferably 2 hours to 4 days. Thereafter, if necessary, excess hydrophobic organic substances are removed, and the resulting micelle solution is subjected to electrolytic treatment using an electrode described below while it is left standing or with slight stirring.

Additionally, a hydrophobic organic substance may be supplemented and added to the micelle solution during the electrolytic treatment, or the micelle solution near the anode may be extracted from the system, and the hydrophobic organic substance may be added to the extracted micelle solution and thoroughly mixed and stirred. Afterwards, a circulation circuit may be installed to return this liquid to the vicinity of the cathode.The electrolytic conditions in this case may be selected as appropriate depending on various situations, but usually the liquid temperature is 0 to 70°C, preferably 20°C. ~30℃, voltage -10,0
~10. OV, preferably -2.0 to 2. OV, current density 10m+A/C1l'' or less, preferably 50~3
00 uA/c11".

When this electrolytic treatment is performed, the redox reaction of the ferrocene derivative proceeds. Focusing on the behavior of Fe ions in ferrocene derivatives, we can see that at the anode, the Fe'' of ferrocene is
e'', the micelles collapse, and particles of hydrophobic organic substances (approximately 600 to 900 particles) are deposited on the anode.
At the cathode, Fe oxidized at the anode! Since + is reduced to Fe'' and returns to the original micelle, membrane forming operations can be performed repeatedly using the same solution.

The new ferrocene derivative used in the method of the present invention has one methyl group in each of the five-membered rings of the ferrocene skeleton, and has a structure with a side chain having a polyoxyethylene group, so it is hydrophobic. It has a high ability to solubilize substances, and furthermore, the efficiency of the above-mentioned redox reaction is very high, and a thin film can be formed in a short time.

Through such electrolytic treatment, a thin film of about 600 to 900 particles of the desired hydrophobic organic substance is formed on the anode.

The supporting salt (supporting electrolyte) used in the method of the present invention is added as necessary to adjust the electrical conductivity of the aqueous medium. The amount of supporting salt added is usually about 0 to 300 times the concentration of the surfactant (micelle forming agent), preferably about 10 to 200 times. Although electrolysis can be performed without adding this supporting salt, in this case, a highly pure thin film containing no supporting salt can be obtained.

In addition, when using a supporting salt, the type of supporting salt is particularly limited as long as it can adjust the electrical conductivity of the aqueous medium without interfering with the formation of micelles or the precipitation of the hydrophobic organic substance on the electrode. There isn't.

Specifically, sulfates (lithium, potassium, sodium, etc.) are commonly used as supporting salts.

salts of rubidium, aluminum, etc.), acetate salts (lithium, potassium, sodium, rubidium, etc.).

salts such as beryllium, magnesium, calcium, strontium, barium, and aluminum).

Halide salts (lithium, potassium, sodium, rubidium, calcium, magnesium, aluminum, etc.) and water-soluble oxide salts (lithium, potassium, sodium, rubidium, calcium, magnesium, aluminum, etc. salts) are suitable.

Further, the electrode used in the method of the present invention may be any metal or conductor that has a higher oxidation potential than ferrocene (+O, l 5 V vs. saturated low-temperature electrode). Specifically, ITO (mixed oxide of indium oxide and tin oxide), platinum, gold,
Examples include silver, grady carbon, conductive metal oxides, and organic polymer conductors.

〔Example〕

Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples.

Production Example 1 (1) In the presence of 16.0 g of anhydrous aluminum chloride, 1°1
12.5 g of dimethylferrocene and 14.6 g of 9-ethoxycarbonylnonanoic acid chloride were reacted in a methylene chloride solvent at room temperature for 2 hours. After the reaction was completed, the following compound was treated with dilute hydrochloric acid and purified using a silica gel column, substituted at the α-position of 1.1'-dimethylferrocene.9.4
The following compound substituted at g and β positions ■13. Obtained Og.

Hs CH3 (2) 9.4 g of compound (2) and 3.0 g of potassium hydroxide were refluxed in an ethanol solvent for 2 hours, and then treated with an acid to obtain 8.3 g of the hydrolyzed compound (2) below.

(3) Compound ■13. Qg and potassium hydroxide4. ], g
After refluxing the mixture in an ethanol solvent for 2 hours, the mixture was treated with an acid to obtain 11.8 g of the hydrolyzed compound (2) below.

(4) In the presence of zinc amalgam prepared from 5.5 g of zinc and 2.3 g of mercuric chloride, 8.3 g of compound (1) was reacted in a mixed solvent of concentrated hydrochloric acid and ethanol at 80°C for 3 hours. 0 Reaction completed. Thereafter, the mixture was extracted with ethyl acetate and purified using a silica gel column to obtain 6.9 g of the following compound (1).

(5) In the presence of a zinc amalgam prepared from 7.7 g of zinc and 3.2 g of mercuric chloride, 11.8 g of compound (1) was reacted in a mixed solvent of concentrated hydrochloric acid and ethanol at 80° C. for 3 hours. After the reaction was completed, the mixture was extracted with ethyl acetate and purified using a silica gel column to obtain 10.4 g of the following compound (1).

The extracted and concentrated product was purified using a silica gel column using a mixed solvent of ethyl acetate and methanol (ethyl acetate: methanol = 3:1), yielding 0.8 g.
The desired compound (2) was obtained with a yield of 34.1%. The results of proton nuclear magnetic resonance ('H-NMR) measurements of this substance are shown in FIG.

CH.

Example 1 Compound ■1. Og and polyethylene glycol (average molecular weight 600) 14.5g with concentrated sulfuric acid 0.2d
The reaction was allowed to take place at °C for 10 hours. After the reaction was completed, treated with water, and then Hxed with water-saturated n-butanol. Example 2 Same as Example 1 except that compound ■ was used instead of compound ■.
The same operation was performed. As a result, the following target compound (2) was obtained in a yield of 0.9 g and a yield of 38.4%. The 'H-NMR measurement results of this substance are shown in FIG.

The elemental analysis values of compounds (1) and (2) are shown below.

Example 3 The ferrocene derivative micellar agent obtained in Example 1 was added to 100 cc of water to make a 2 mM solution, and this micelle solution 20
0.1 g of phthalocyanine (manufactured by Tokyo Kasei ■) was added to the cc and stirred with ultrasonic waves for 10 minutes to disperse and solubilize. Furthermore, after stirring with a stirrer for two days and nights, the obtained dispersed and solubilized micelle solution was centrifuged at 2000 rpm for 30 minutes. From the visible absorption spectrum of this supernatant,
It was confirmed that the phthalocyanine was dispersed, and the solubilization ability of the micelle agent was determined to be 9.9mM/2mM based on the absorbance.
It was found to be an M micelle agent.

Add 0.1M lithium bromide to this dispersed and solubilized micelle solution.
and stirred with a stirrer for 10 minutes. Using this solution as an electrolyte, constant potential electrolysis was performed at 25° C. and an applied voltage of 0.5 V using an ITO transparent glass electrode as an anode, a platinum plate as a cathode, and a saturated red electrode as a reference electrode. The current density at this time was 10.2 u A/cij, the current application time was 30 minutes, and the current application amount was 0.02 coulombs (C).

As a result, a thin film of phthalocyanine was obtained on the ITO transparent glass electrode. Since the absorption spectrum of phthalocyanine on this ITO transparent glass electrode and the absorption spectrum of the dispersed solubilized micelle solution matched, it was determined that the thin film on the ITO transparent glass electrode was phthalocyanine, and the film thickness was 2.6 μm from the absorbance. Ta.

Example 4 The ferrocene derivative micellar agent obtained in Example 2 was added to 100 cc of water to make a 2 mM solution, and this micelle solution 2
0.1 g of phthalocyanine (manufactured by Tokyo Kasei) in 0 cc
In addition, the mixture was stirred using ultrasound for 10 minutes to disperse and solubilize. Furthermore, after stirring with a stirrer for two days and nights, the obtained dispersed and solubilized micelle solution was centrifuged at 2000 rpm for 30 minutes. From the visible absorption spectrum of this supernatant, it was confirmed that phthalocyanine was dispersed, and from the absorbance, the solubilization ability of the micelle-forming agent was 8.6mM.
It was found to be a 72mM micelle agent.

Add 0.1M lithium bromide to this dispersed and solubilized micelle solution.
and stirred with a stirrer for 10 minutes. Using this solution as an electrolyte, constant potential electrolysis was carried out at 25° C. and an applied voltage of 0.5 μ using an ITO transparent glass electrode as an anode, a platinum plate as a cathode, and a saturated Euca electrode as a reference electrode. At this time, the current density was 11.6 μA/d, the current application time was 30 minutes, and the current application amount was 0.03 G.

As a result, a thin film of phthalocyanine was obtained on the ITO transparent glass electrode. Since the absorption spectrum of phthalocyanine on this ITO transparent glass electrode matches the absorption spectrum of the dispersed solubilized micelle solution, it was determined that the thin film on the ITO transparent glass electrode was phthalocyanine, and the film thickness was 2.3 μm from the absorbance. Ta.

Comparative Example 1 A ferrocene derivative micellar agent represented by the following structural formula (manufactured by the method described in International Publication WO3B107538) was added to 100 cc of water to make a 2 mM solution, and phthalocyanine (manufactured by Tokyo Kasei ■) was added to 20 cc of this micellar solution. 0.
1 g was added and stirred using ultrasound for 10 minutes to disperse and solubilize. Furthermore, after stirring with a stirrer for two days and nights,
The obtained dispersed solubilized micelle solution was heated at 2000 rpi for 30 min.
Centrifugation was performed for minutes. From the visible absorption spectrum of this supernatant, it was confirmed that phthalocyanine was dispersed, and from the absorbance, the solubilizing ability of the micelle-forming agent was 8.2.
It was found to be an mM/2mM micelle agent.

Add 0, 1 lithium bromide to this dispersed and solubilized micelle solution.
The mixture was added to a concentration of M and stirred with a stirrer for 10 minutes. Using this solution as an electrolyte, constant potential electrolysis was carried out at 25° C. and an applied voltage of 0.5 μ using an ITO transparent glass electrode as an anode, a platinum plate as a cathode, and a saturated copper electrode as a reference electrode. The current density at this time was 11.3 uA/cTA
The energization time was 30 minutes, and the energization amount was 0.02C.

As a result, a thin film of phthalocyanine was obtained on the ITO transparent glass electrode. Since the absorption spectrum of phthalocyanine on this IT○ transparent glass electrode and the absorption spectrum of the dispersed solubilized micelle solution match, it is determined that the thin film on the ITO transparent glass electrode is phthalocyanine, and the film thickness is 1.9 μm based on the absorbance. understood.

Comparative Example 2 A ferrocene derivative micelle agent represented by the following structural formula [phase] (manufactured by the method described in International Publication WO 3810753B) was added to 100 cc of water to make a 2 mM solution, and 20 cc of this micellar solution was added with phthalocyanine (manufactured by Tokyo Kasei Corporation). ) was added and stirred using ultrasound for 10 minutes to disperse and solubilize. Furthermore, after stirring with a stirrer for two days and nights, the obtained dispersed and solubilized micelle solution was centrifuged at 200 rpm for 30 minutes. From the visible absorption spectrum of this supernatant, it was confirmed that phthalocyanine was dispersed, and from the absorbance, the solubilization ability of the micelle-forming agent was 4.
It was found to be a 0mM/2mM micelle agent.

Add 0.1M lithium bromide to this dispersed and solubilized micelle solution.
and stirred with a stirrer for 10 minutes. Using this solution as an electrolyte, constant potential electrolysis was performed at 25° C. and an applied voltage of 0.5 V using an ITO transparent glass electrode as an anode, a platinum plate as a cathode, and a saturated copper electrode as a reference electrode. At this time, the current density was 17.6 uA/cd, the current application time was 30 minutes, and the current application amount was 0.03C.

As a result, a thin film of phthalocyanine was deposited on the ITOyL bright glass electrode. Since the absorption spectrum of phthalocyanine on this ITO transparent glass electrode and the absorption spectrum of the dispersed and solubilized micelle solution matched, it was determined that the thin film on the ITO transparent glass electrode was phthalocyanine, and the film thickness was 2.1 μm from the absorbance. Ta.

〔Effect of the invention〕

The ferrocene derivative of the present invention is a compound of ferrocene derivative having one methyl group in each five-membered ring constituting the ferrocene skeleton, and can be used as a surfactant (micellar agent), a catalyst, a combustion improver, and a flotation agent. .

It can be used for various purposes such as lubricating aid 2 dispersant and liquid crystal. In particular, when this ferrocene derivative is used as a surfactant (micelle forming agent), it forms micelles in an aqueous solution system.
It is possible to very easily solubilize various hydrophobic organic substances such as pigments such as phthalocyanine, which have a wide range of applications, and various hydrophobic polymers. Further, by adding this surfactant (micelle forming agent) and following the method of the present invention which utilizes aggregation and dispersion of micelles by aqueous electrolysis, an extremely thin organic thin film can be quickly formed.

Furthermore, since the above-mentioned surfactant has excellent redox efficiency, the film-forming ability is extremely high, and the film can be formed in a short time.

The organic thin film formed by the method of the present invention is expected to be effectively used in various fields including photoelectric conversion materials, photosensitive materials, and solar cells.

[Brief explanation of drawings]

Figure 1 shows the 'H-
Figure 2 shows 'H-NMR of the ferrocene derivative obtained in Example 2. Patent applicant Idemitsu Kosan Co., Ltd.

Claims (4)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, [In the formula, Y indicates -O- or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, n is an integer from 6 to 13, m is 5 Indicates a real number between .0 and 30.0. ] A novel ferrocene derivative represented by (2) A surfactant containing the novel ferrocene derivative according to claim 1. (3) A method for solubilizing a hydrophobic organic substance, which comprises solubilizing the hydrophobic organic substance in an aqueous medium with a surfactant containing the novel ferrocene derivative according to claim 1. (4) A hydrophobic organic substance is solubilized in an aqueous medium with a surfactant containing the novel ferrocene derivative according to claim 1, and the resulting micellar solution is electrolyzed to coat the hydrophobic organic substance on an electrode. A method for producing an organic thin film, the method comprising forming a thin film.