JPH0725885A - Trialkoxy(thienylalkyl)silane and its production - Google Patents

Abstract

PURPOSE:To easily obtain a trialkoxy(thienylakyl)silane useful as a coupling agent for electrically conductive polymeric material and an inorganic material by reacting a specific thienylalkene derivative with a specific trialkoxysilane. CONSTITUTION:This silane compound of the formula I [R1 to R3 are H, 1-12C alkyl or 1-12C alkoxy provided that at least one of R<1> and R<3> is H; R<4> to R<6> are H or 1-6C alkyl; R<7> to R<9> are 1-6C alkyl; (n) is 0-10) or the formula II (R<1> is H) is produced by reacting a thienylalkene derivative of the formula III or the formula IV with a trialkoxysilane of the formula V.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to trialkoxy (thienylalkyl) silane which acts as a coupling agent for a conductive polymer material and an inorganic material and a method for producing the same.

[0002]

2. Description of the Related Art A compound having a polymerizable functional group and a trialkoxysilyl group acts as a coupling agent between an organic polymer and an inorganic material such as glass and plays a very important role in the development of advanced composite materials. There is. For example, vinyl silanes are used to improve the mechanical strength of general-purpose resins such as polyethylene, polypropylene, and polystyrene.

As one of such silane coupling agents, a compound in which a conductive polymer monomer and a trialkylsilyl group are bonded is used to form a permanent conductive layer on the surface of an inorganic material such as glass or silicon wafer. Are being studied for use as coupling agents. So far, N- (3- (trimethoxysilyl) propyl) pyrrole (J. Am. Chem. Soc., 104 , 2031-2034 (1) for modifying the surface of a platinum electrode or an n-type silicon electrode with a polypyrrole film has been used.
982)), a pyrrolidyl group-containing silane coupling agent for forming a conductive layer on a glass substrate (International Publication No. WO 92
/ 06100) etc. have been reported. A polypyrrole film can be formed by covalently bonding these compounds using an OH group on a silicon wafer or a glass substrate and then copolymerizing them with pyrrole.

However, the pyrrole to be copolymerized with these compounds has a small number of polypyrrole derivatives reported because it is difficult to introduce a substituent at a position other than the nitrogen atom. As an example of the polypyrrole derivative reported so far, poly (N-alkylpyrrole) (S having an alkyl group introduced at the nitrogen atom position of the pyrrole ring) (S
ynth.Met., 15 , 49-58 (1986)) and poly (3-alkylpyrrole) with an alkyl group introduced at the 3-position of the pyrrole ring (Ma
kromol.Chem., Rapid Commun., 10 , 103-108 (1989)), etc., but these compounds have lower electric conductivity than unsubstituted polypyrrole and are similar to unsubstituted polypyrrole. There are problems such as low stability in the dedoped state.

On the other hand, thiophene, which is a 5-membered heterocyclic ring having a sulfur atom instead of a nitrogen atom, can easily be introduced with various functional groups at the 3-position. It has been reported that a polythiophene derivative having useful properties can be obtained without impairing the properties of the unsubstituted polythiophene that is stable in both the doped state and the doped state. An example of such a polythiophene derivative is poly (3-alkylthiophene), which not only dissolves in an organic solvent but also exhibits solvatochromism and thermochromism.
ournal of Applied Physics, 27 , L716-L718 (1988)) and self-doped polymers that do not require exogenous dopants,
Poly [2- (3-thienyl) ethanesulfonic acid] and poly [4- (3-thienyl) butanesulfonic acid] (Synthet
ic Metals, 20 , 151-159 (1987)) and the like.

[0006]

As described above, conductive polymers that can be composited with an inorganic material by a conventionally known silane coupling agent are limited to polypyrrole derivatives, and the number of these derivatives is small. However, it has a drawback that it cannot be used except for the purpose of imparting conductivity to the surface of an inorganic material such as silicon or glass. Therefore, an object of the present invention is to develop a silane coupling agent capable of forming a composite of a thiophene derivative having useful properties and an inorganic material.

[0007]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventor has found that a trialkoxysilyl group can be easily introduced into a thiophene derivative by reacting a specific thiophene derivative with trialkoxysilane. The present invention has been completed and the present invention has been completed. That is, the present invention is represented by the general formula (I)

[Chemical 6] (In the formula, R ¹ , R ² and R ³ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, provided that either R ¹ or R ³ One is always a hydrogen atom, R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ⁷ , R ⁸ and R ⁹ are each independently a carbon atom. 1
Represents an alkyl group of 6 to 6. n is an integer of 0 to 10. ) Or general formula (II)

[Chemical 7] (In the formula, R ¹ represents a hydrogen atom, and R ² and R ³ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R ⁴ and R ⁵
And R ⁶ are each independently a hydrogen atom or 1 to 6 carbon atoms.
Is represented by R ⁷ , R ⁸ and R ⁹ each independently represents an alkyl group having 1 to 6 carbon atoms. n is 0 to 10
Is an integer. And a trialkoxy (thienylalkyl) silane represented by the general formula (III)

[Chemical 8] (In the formula, R ¹ , R ² and R ³ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, provided that either R ¹ or R ³ One is always a hydrogen atom, R ⁴ , R ⁵ and R ⁶
Each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 0 to 10. ) Or general formula (IV)

[Chemical 9] (In the formula, R ¹ represents a hydrogen atom, and R ² and R ³ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R ⁴ and R ⁵
And R ⁶ are each independently a hydrogen atom or 1 to 6 carbon atoms.
Represents an alkyl group, and n is an integer of 0 to 10. )
With a thienylalkene derivative represented by the general formula (V)

[Chemical 10] (In the formula, R ⁷ , R ⁸ and R ⁹ each independently represent an alkyl group having 1 to 6 carbon atoms.) A trialkoxysilane represented by the formula: A method for producing silane is provided.

The present invention will be described in detail below. The trialkoxy (thienylalkyl) silane provided by the present invention is represented by the above general formula (I) or general formula (II), and preferred examples of the compound include R ¹ , R ² and R ³ each independently. A hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
R ⁴ , R ⁵ and R ⁶ are hydrogen atoms, R ⁷ , R ⁸ and R ⁹ are each independently an alkyl group having 1 to 4 carbon atoms, and n is an integer of 1 to 4. Especially R ⁷ , R
Particularly preferred are those in which ⁸ and R ⁹ are the same alkyl group.

Particularly preferred specific examples of the compound of the present invention represented by the general formula (I) are trimethoxy [3- (3-thienyl) propyl] silane and triethoxy [3- (3-
Thienyl) propyl] silane, tripropyloxy [3
-(3-thienyl) propyl] silane, tributoxy [3- (3-thienyl) propyl] silane, triethoxy [3- (2-methyl-3-thienyl) propyl] silane, triethoxy [3- (4-methyl-3) -Thienyl)
Propyl] silane, triethoxy [3- (5-methyl-
3-thienyl) propyl] silane, triethoxy [3-
(4-Ethyl-3-thienyl) propyl] silane, triethoxy [3- (4-butyl-3-thienyl) propyl] silane, triethoxy [3- (4-hexyl-3-)
Thienyl) propyl] silane, trimethoxy [4- (3
-Thienyl) ethyl] silane, triethoxy [4- (3
-Thienyl) ethyl] silane, trimethoxy [4- (3
-Thienyl) butyl] silane, triethoxy [4- (3
-Thienyl) butyl] silane, trimethoxy [5- (3
-Thienyl) pentyl] silane, triethoxy [5-
(3-thienyl) pentyl] silane, trimethoxy [6
Examples thereof include-(3-thienyl) hexyl] silane and triethoxy [6- (3-thienyl) hexyl] silane.

Particularly preferred specific examples of the compound of the present invention represented by the general formula (II) are trimethoxy [3- (2-thienyl) propyl] silane and triethoxy [3- (2-
Thienyl) propyl] silane, tripropyloxy [3
-(2-thienyl) propyl] silane, tributoxy [3- (2-thienyl) propyl] silane, triethoxy [3- (3-methyl-2-thienyl) propyl] silane, triethoxy [3- (4-methyl-2) -Thienyl)
Propyl] silane, triethoxy [3- (3-ethyl-
2-thienyl) propyl] silane, triethoxy [3-
(3-Butyl-2-thienyl) propyl] silane, triethoxy [3- (3-hexyl-2-thienyl) propyl] silane, trimethoxy [4- (2-thienyl) ethyl] silane, triethoxy [4- (2- Thienyl) ethyl] silane, trimethoxy [4- (2-thienyl) butyl] silane, triethoxy [4- (2-thienyl) butyl] silane, trimethoxy [5- (2-thienyl) pentyl] silane, triethoxy [5- ( 2-thienyl) pentyl] silane, trimethoxy [6- (2-thienyl)
Hexyl] silane, triethoxy [6- (2-thienyl) hexyl] silane and the like can be mentioned.

Specific examples of the thienylalkene derivative represented by the general formula (III), which is a raw material for the compound of the present invention represented by the general formula (I), include 3- (3-thienyl) -1-propene and 3 -(2-Methyl-3-thienyl) -1-propene, 3- (4-methyl-3-thienyl) -1-propene, 3- (5-methyl-3-thienyl) -1-propene, 3- ( 4-Ethyl-3-thienyl) -1-propene, 3- (4-butyl-3-thienyl) -1-propene, 3- (4-hexyl-3-thienyl) -1-propene, 4- (3- Thienyl) -1-butene, 5- (3-thienyl) -1-pentene, 6- (3-thienyl) -1-
Hexene and the like can be mentioned.

Specific examples of the thienylalkene derivative represented by the general formula (IV), which is the starting material for the compound of the present invention represented by the general formula (II), include 3- (2-thienyl) -1-propene and 3 -(3-Methyl-2-thienyl) -1-propene, 3- (4-methyl-2-thienyl) -1-propene, 3- (3-ethyl-2-thienyl) -1-propene, 3- ( 3-Butyl-2-thienyl) -1-propene, 3- (3-hexyl-2-thienyl) -1-propene, 4- (2-thienyl) -1-butene, 5- (2-thienyl) -1. -Pentene, 6- (2-thienyl) -1-
Hexene and the like can be mentioned.

These thienylalkene derivatives can be produced, for example, by reacting a 3-bromothiophene derivative or a 2-bromothiophene derivative with n-butyllithium and then reacting with a corresponding ω-bromo-1-alkene. .

At least one selected from the above thienylalkene derivative group is a trialkoxysilane represented by the general formula (V) in the presence of a transition metal complex catalyst in an atmosphere of an inert gas such as nitrogen or argon. The corresponding trialkoxy (thienylalkyl) silanes are obtained by reacting

Specific preferred examples of the trialkoxysilane represented by the general formula (V) include trimethoxysilane, triethoxysilane, tripropyloxysilane, triisopropyloxysilane, tributoxysilane and triisobutoxysilane. be able to.

The amount of trialkoxysilane used in the reaction is usually equimolar or more with respect to the thienylalkene derivative, but preferably 1.5 to 5 times the molar amount.
Examples of transition metal complexes used as catalysts for this reaction include platinum catalysts such as chloroplatinic acid and bis (triphenylphosphine) platinum chloride, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium chloride, acetic acid. Palladium, palladium catalysts such as [1,1′-bis (diphenylphosphine) ferrocene] palladium chloride, cobalt catalysts such as cobalt carbonyl and cyclopentadienyl cobalt dicarbonyl, rhodium catalysts such as tris (triphenylphosphine) rhodium chloride, Ruthenium catalysts such as tris (triphenylphosphine) ruthenium dichloride, osmium catalysts such as osmium tetroxide, bis (1,5-cyclooctadiene) nickel, bis (acetylacetonato) nickel and dichloro [1,3-bis ( Gif Examples thereof include nickel catalysts such as phenylphosphino) propane] nickel. Of these transition metal complex catalysts, platinum catalysts are preferred.

The amount of the transition metal complex catalyst used in the reaction is usually an equimolar amount to 1 with respect to the thienylalkene derivative.
× 10 ^-4 times the molar amount, preferably ^{1x10 -1} to ^{1x10 -2}
Use a double molar amount.

The above-mentioned reaction is usually carried out in an organic solvent, and examples of the organic solvent include nitriles such as acetonitrile, propionitrile and butyronitrile, ethers such as diethyl ether, tetrahydrofuran and dioxane,
Examples thereof include esters such as ethyl acetate, butyl acetate, methyl propionate, and other non-aqueous solvents.
Of these, nitriles such as acetonitrile are preferable. It is desirable to use those organic solvents that have been distilled in advance under an atmosphere of an inert gas such as nitrogen or argon.

The reaction temperature and time differ depending on the solvent used and cannot be decided unconditionally, but when acetonitrile is used as the solvent, it is usually 10 to 82.
At a temperature of 30 ° C., preferably 30 to 70 ° C., for 1 to 48 hours,
The reaction is preferably carried out for 2 to 12 hours.

After completion of the reaction, the solvent and unreacted trialkoxysilane are distilled off by using a means such as a rotary evaporator, and a mixture such as a residue or ether, if necessary, is added and stirred to obtain a catalyst or the like by filtration. The precipitate is removed and the filtrate is distilled under reduced pressure to obtain trialkoxy (thienylalkyl) silane.

By thus reacting the thienylalkene derivative with the trialkoxysilane, trialkoxy (thienylalkyl) silane can be produced in high yield and high selectivity with almost no side reaction. .

Since the compound represented by the general formula (I) obtained by the present invention has a thienyl group, it can be easily copolymerized with various thiophene derivatives. Therefore, poly (3-alkylthiophenes) exhibiting electrochromism and thermochromism (Japanese Journal of
Applied Physics, 27 , L716-L718 (1988)) and a self-doped polymer, poly [2-
(3-thienyl) ethanesulfonic acid] and poly [4-
(3-thienyl) butane sulfonic acid] (Synthetic Meta
ls, 20 , 151-159 (1987)) and other polythiophene derivatives having useful properties.

[0023]

EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples. Example 1 A 500 ml four-necked flask was equipped with a thermometer, a dropping funnel and a condenser, and the inside of the container was replaced with nitrogen. With 10.0 g of 3- (3-thienyl) -1-propene (0.081 mol)
0.73 g of hexachloroplatinic (IV) acid hexahydrate (0.0014 mol) was added, and 300 ml of acetonitrile was added and dissolved. While stirring the solution, 36.0 g of triethoxysilane (0.22 mol) was added through the dropping funnel. After the addition, the temperature of the reaction solution was raised to 50 ° C. and the reaction was carried out for 4 hours.
After completion of the reaction, the solvent and unreacted triethoxysilane are distilled off, the insoluble matter is removed from the residue by filtration, and the filtrate is distilled under reduced pressure to obtain 12.5 g of triethoxy [3- (3-thienyl) propyl] silane. Obtained. (Bp.115 ° C./3 mmHg purification yield 55%) ¹ H NMR (CDCl ₃ ): 0.67 (2H, m), 1.23
(9H, t), 1.75 (2H, m), 2.66 (2H, m), 3.81
(6H, q), 6.93 (2H, m), 7.22 (1H, m) ¹³ C NMR (CDCl ₃ ): 10.2, 18.3, 24.0, 33.
5, 58.4, 120.4, 125.1, 128.3, 142.7

Example 2 In the same manner as in Example 1 except that 3- (2-thienyl) -1-propene was used in place of 3- (3-thienyl) -1-propene in Example 1, 10.5 g of triethoxy [3- (2-thienyl) propyl] silane was obtained. (Bp.115 ° C./3 mmHg, purification yield 45%) ¹ H NMR (CDCl ₃ ): 0.67 (2H, m), 1.23
(9H, t), 1.75 (2H, m), 2.78 (2H, m), 3.80
(6H, q), 6.88 (1H, m), 6.98 (1H, m), 7.18
(1H, m) ¹³ C NMR (CDCl ₃ ): 10.2, 18.3, 24.2, 32.
5, 58.5, 122.8, 124.1, 126.6, 145.3

Example 3 A 200 ml four-necked flask was equipped with a thermometer, a dropping funnel and a condenser, and the inside of the container was replaced with nitrogen. With 3.0 g of 6- (3-thienyl) -1-hexene (0.018 mol)
0.30 g of hexachloroplatinic (IV) acid hexahydrate (0.00058
Mol), and 100 ml of acetonitrile was added and dissolved. With stirring the solution, 11.0 g of trimethoxysilane (0.090 mol) was added through a dropping funnel.
After the addition, the temperature of the reaction solution was raised to 70 ° C. and the reaction was performed for 10 hours. After completion of the reaction, the solvent and unreacted trimethoxysilane were distilled off under reduced pressure, a small amount of diethyl ether was added to the residue and the mixture was stirred, and the insoluble matter was removed by filtration, and 1.5 g of trimethoxy [6- (3- (3- Thienyl) hexyl] silane was obtained. (Bp. 145-150 ° C./1 mmHg, purification yield 30%) ¹ H NMR (CDCl ₃ ): 0.68 (2H, m), 1.1-1.7
(8H, m), 2.65 (2H, m), 3.50 (9H, s), 6.93
(2H, m), 7.22 (1H, m) ¹³ C NMR (CDCl ₃ ): 11.8, 24.0, 29.5, 30.
6, 32.0, 33.5, 50.5, 119.8, 125.0, 128.3, 143.2

Example 4 A 500 ml four-necked flask was equipped with a thermometer, a dropping funnel and a condenser, and the inside of the container was replaced with nitrogen. To this was added 10.0 g of 3- (3-methyl-2-thienyl) -1-propene (0.
(072 mol) and 0.62 g of hexachloroplatinum (IV) acid hexahydrate (0.0012 mol) were added, and 300 ml of acetonitrile was added and dissolved. While stirring the solution, 33.0 g of triethoxysilane (0.20 mol) was added through the dropping funnel. After the addition, the temperature of the reaction solution was raised to 50 ° C. and the reaction was carried out for 4 hours. After the reaction was completed, the solvent and unreacted triethoxysilane were distilled off under reduced pressure, a small amount of diethyl ether was added to the residue and the mixture was stirred, and the insoluble matter was removed by filtration, and the filtrate was distilled under reduced pressure to obtain 12.0 g of triethoxysilane. [3- (3-Methyl-2-thienyl) propyl] silane was obtained. (Bp. 135-145 ° C./3 mmHg, purification yield 55%) ¹ H NMR (CDCl ₃ ): 0.67 (2H, m), 1.23
(9H, t), 1.75 (2H, m), 2.20 (3H, s), 2.78
(2H, m), 3.80 (6H, q), 6.75 (1H, d), 6.85
(1H, d) ¹³ C NMR (CDCl ₃ ): 10.2, 12.7, 18.3, 24.
2, 32.5, 58.5, 123.3, 129.2, 135.7, 136.6

Example 5 A 500 ml four-necked flask was equipped with a thermometer, a dropping funnel and a condenser, and the inside of the container was replaced with nitrogen. With 10.0 g of 3- (3-thienyl) -1-propene (0.081 mol)
0.73 g of hexachloroplatinic (IV) acid hexahydrate (0.0014 mol) was added, and 300 ml of acetonitrile was added and dissolved. While stirring the solution, 45.0 g of tripropyloxysilane (0.22 mol) was added through a dropping funnel. After the addition, the temperature of the reaction solution was raised to 60 ° C. and the reaction was carried out for 8 hours. After completion of the reaction, the solvent and unreacted tripropyloxysilane were distilled off under reduced pressure, a small amount of diethyl ether was added to the residue and the mixture was stirred, and the insoluble matter was removed by filtration. Tripropyloxy [3- (3
-Thienyl) propyl] silane was obtained. (Bp 140-150 ° C./2 mmHg, purification yield 45%) ¹ H NMR (CDCl ₃ ): 0.67 (2H, m), O.92
(9H, t), 1.57 (6H, m), 1.75 (2H, m), 2.66
(2H, m), 3.75 (6H, t), 6.93 (2H, m), 7.22
(1H, m) ¹³ C NMR (CDCl ₃ ): 10.2, 10.3, 24.0, 25.
9, 33.5, 65.2, 120.4, 125.1, 128.3, 142.7

Example 6 0.3 g of triethoxy [3- (3-thienyl) propyl] silane synthesized in Example 1 in a 100 ml beaker.
Add 47.5 ml of ethyl alcohol and 2.5 ml
Of acetic acid was added and dissolved. An n-type silicon wafer (30 mm x 30 mm x 1 mm: the surface of which was previously etched with hydrofluoric acid for 5 seconds, then immersed in a 10 M aqueous sodium hydroxide solution for 60 seconds, and then washed with distilled water and acetone in this solution ) Was dipped for 72 hours to modify the surface. Using the n-type silicon wafer thus prepared as an anode, 0.01 M of 3-dodecylthiophene was dissolved.
By electropolymerization in a 1 M tetraethylammonium tetrafluoroammonium salt / acetonitrile solution by a known method, 3-dodecylthiophene and triethoxy [3- (3) which are substantially close to poly (3-dodecylthiophene) on the surface of a silicon wafer are obtained. -Thienyl) propyl]
Coated with a copolymer of silane. Further, the obtained silicon wafer was immersed in methanol to dedope the copolymer on the surface. The color of the obtained copolymer film was reddish brown at 25 ° C., but when it was heated to 90 ° C. or higher, it changed to yellow brown, showing thermochromism.

Example 7 In a 100 ml beaker, 0.3 g of triethoxy [3- (3-methyl-2-thienyl) propyl] silane synthesized in Example 4 was placed, and 47.5 ml of ethyl alcohol and 2.5 ml of acetic acid were added. In addition, it dissolved. An n-type silicon wafer (30 mm x 30 mm x 1 mm: the surface of which was previously etched with hydrofluoric acid for 5 seconds, then immersed in a 10 M aqueous sodium hydroxide solution for 60 seconds, and then washed with distilled water and acetone in this solution ) Was dipped for 72 hours to modify the surface. Using the n-type silicon wafer thus prepared as an anode, electrolytic polymerization was performed by a known method in a 0.1 M tetraethylammonium tetrafluoroborate tetraethylammonium salt / acetonitrile solution in which 0.01 M 3-dodecylthiophene was dissolved. The surface of the wafer is substantially close to poly (3-dodecylthiophene), 3-dodecylthiophene and triethoxy [3- (3-methyl-2)
Coated with -thienyl) propyl] silane copolymer.
Further, the obtained silicon wafer was immersed in methanol to dedope the copolymer on the surface. The color of the obtained copolymer film was reddish brown at 25 ° C., but when it was heated to 90 ° C. or higher, it changed to yellow brown, showing thermochromism.

[0030]

Industrial Applicability According to the present invention, a silane coupling agent having a thienyl group which is easy to copolymerize with a thiophene derivative is provided, and the agent can be produced in high yield and high selectivity. As a result, it is easy to introduce functional groups having various functions into the side chains of thiophene, so that not only can a conductive layer be formed on the surface of an inorganic material such as glass or silicon electrodes, but also electrochromic layers and thermostats can be formed. It is possible to form a thin film having various functions such as a chromic layer.

Claims (2)

[Claims] 1. A compound represented by the general formula (I): (In the formula, R ¹ , R ² and R ³ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, provided that either R ¹ or R ³ One is always a hydrogen atom, R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ⁷ , R ⁸ and R ⁹ are each independently a carbon atom. 1
Represents an alkyl group of 6 to 6. n is an integer of 0 to 10. ) Or general formula (II) (In the formula, R ¹ represents a hydrogen atom, and R ² and R ³ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R ⁴ and R ⁵
And R ⁶ are each independently a hydrogen atom or 1 to 6 carbon atoms.
Is represented by R ⁷ , R ⁸ and R ⁹ each independently represents an alkyl group having 1 to 6 carbon atoms. n is 0 to 10
Is an integer. ) A trialkoxy (thienylalkyl) silane represented by the formula: 2. A compound represented by the general formula (III): (In the formula, R ¹ , R ² and R ³ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, provided that either R ¹ or R ³ One of them is always a hydrogen atom, R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 0 to 10) or a general formula ( IV) [Chemical 4] (In the formula, R ¹ represents a hydrogen atom, and R ² and R ³ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R ⁴ and R ⁵
And R ⁶ are each independently a hydrogen atom or 1 to 6 carbon atoms.
Represents an alkyl group, and n is an integer of 0 to 10. )
And a thienylalkene derivative represented by the general formula (V): The trialkoxysilane represented by the formula (wherein R ⁷ , R ⁸ and R ⁹ each independently represents an alkyl group having 1 to 6 carbon atoms) is reacted with the trialkoxysilane according to claim 1. Method for producing alkoxy (thienylalkyl) silane.