ELECTROCHROMIC MATERIALS
First Claim
1. A method for synthesizing a desired product, the desired product comprising 2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoroethoxy)-thiophene, a monomer suitable for polymerization to achieve a fluorinated electrochromic polymer exhibiting a green color in a first state and a red color in a second state, the method comprising the steps of:
- (a) producing a first intermediate reagent, the first intermediate reagent comprising 2,5-dibromo-3,4-bis-(2,2,2-trifluoroethoxy)-thiophene, by;
(i) providing a first solution comprising a first precursor, the first precursor comprising 3,4-bis-(2,2,2-trifluoroethoxy)-thiophene; and
(ii) heating the first solution to facilitate a reaction that produces the first intermediate reagent; and
(b) producing the desired product by heating a second solution comprising the first intermediate reagent and a substituted thiophene, to facilitate a reaction that produces the desired product.
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Abstract
Green electrochromic (EC) materials based on thiophene, and a green EC material based on pyrazine are disclosed. A first thiophene derivative (2,3-Di-thiophen-2-yl-thieno[3,4-b]pyrazine), which was previously investigated as a nonlinear optical material, is here disclosed for its use as an EC material and for its incorporation into an EC device. Synthesis of two new thiophene derivatives (2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene and 2,5-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene), and a new pyrazine derivative (2,3-dibenzyl-5,7-di(thien-2-yl) thieno[3,4-b]pyrazine) are also disclosed, since these materials are all able to selectively change state to appear a green color and can be polymerized to achieve a green EC polymer.
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Citations
19 Claims
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1. A method for synthesizing a desired product, the desired product comprising 2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoroethoxy)-thiophene, a monomer suitable for polymerization to achieve a fluorinated electrochromic polymer exhibiting a green color in a first state and a red color in a second state, the method comprising the steps of:
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(a) producing a first intermediate reagent, the first intermediate reagent comprising 2,5-dibromo-3,4-bis-(2,2,2-trifluoroethoxy)-thiophene, by; (i) providing a first solution comprising a first precursor, the first precursor comprising 3,4-bis-(2,2,2-trifluoroethoxy)-thiophene; and (ii) heating the first solution to facilitate a reaction that produces the first intermediate reagent; and (b) producing the desired product by heating a second solution comprising the first intermediate reagent and a substituted thiophene, to facilitate a reaction that produces the desired product. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14)
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15. A method for synthesizing a fluorinated electrochromic monomer suitable for polymerization to achieve a fluorinated electrochromic polymer, the fluorinated electrochromic monomer being a fluorinated derivative of 2,5-di(thien-2-yl)-3,4-dihydroxy-thiophene, the fluorinated derivative corresponding to 2,5-di(thien-2-yl)-3,4-di(R-oxy)-thiophene, with R comprising a fluorinated functional group, the method comprising the steps of:
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(a) producing a first intermediate reagent comprising a fluorinated derivative of 3,4-dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester, the fluorinated derivative corresponding to 3,4-bis-(R-oxy)-thiophene-2,5-dicarboxylic acid dimethyl ester, by performing the steps of; (i) providing a first solution comprising 3,4-dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester and a fluorinated alcohol comprising R, the fluorinated functional group; and (ii) heating the first solution to facilitate a reaction that will produce the first intermediate reagent; (b) producing a second intermediate reagent comprising a fluorinated derivative of 3,4-dihydroxy-thiophene-2,5-dicarboxylic acid, the fluorinated derivative corresponding to 3,4-bis-(R-oxy)-thiophene-2,5-dicarboxylic acid, by performing the steps of; (i) adding the first intermediate reagent to a second solution; and (ii) heating the second solution to facilitate a reaction that will produce the second intermediate reagent; (c) producing a third intermediate reagent comprising a fluorinated derivative of 3,4-dihydroxy-thiophene, the fluorinated derivative corresponding to 3,4-bis-(R-oxy)-thiophene, by performing the steps of; (i) adding the second intermediate reagent to a third solution; and (ii) heating the third solution to facilitate a reaction that will produce the third intermediate reagent; (d) producing a fourth intermediate reagent comprising a fluorinated derivative of 2,5-dibromo-3,4-dihydroxy-thiophene, the fluorinated derivative corresponding to 2,5-dibromo-3,4-bis-(R-oxy)-thiophene, by performing the steps of; (i) adding the third intermediate reagent to a fourth solution; and (ii) heating the fourth solution to facilitate a reaction that will produce the fourth intermediate reagent; and (e) using the fourth intermediate reagent to produce the fluorinated derivative of 2,5-di(thien-2-yl)-3,4-dihydroxy-thiophene by; (i) adding the fourth intermediate reagent to a fifth solution comprising a substituted thiophene; and (ii) heating the fifth solution to facilitate a reaction that will produce the fluorinated derivative of 2,5-di(thien-2-yl)-3,4-dihydroxy-thiophene. - View Dependent Claims (16, 17, 18)
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19. A method for synthesizing a desired product, the desired product comprising 2,5-(2,3-dihydro-thieno[3,4][1,4]dioxin-5-yl)-3,4-di(2,2,2-trifluoroethoxy)-thiophene, a monomer suitable for polymerization to achieve a fluorinated electrochromic polymer exhibiting a green color in a first state and a purple color in a second state, the method comprising the steps of:
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(a) providing a first solution comprising a first intermediate reagent and a second intermediate reagent, the first intermediate reagent comprising 2,5-dibromo-3,4-bis-(2,2,2-trifluoroethoxy)-thiophene, and the second intermediate reagent comprising a substituted ethylenedioxyl thiophene; and (b) heating the first solution to facilitate a reaction that will produce the desired product.
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Specification