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US 7,442,759 B2Granted
Water-soluble polythiophene polymers
AssigneeRieke Metals, Inc.
InventorReuben Rieke
Life of this patent
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Abstract
The invention provides a water-soluble polymer having formula I: where R1 and R2 are independently —H, -alkylCO2A, —(CH2)n-aryl-(CH2)nCO2A, —(CH2)n-heterocycle-(CH2)nCO2A, or —(CH2)n-cycloalkyl-(CH2)nCO2A, where n is an integer from 0 to 200, and A is an alkali metal cation, with the proviso that only one of R1 and R2 is —H. Methods of preparing the water-soluble polymers and thin films prepared therefrom are also described.
Claims20
A method of forming a water-soluble polymer having formula I:
- wherein R1 and R2 are independently —H, -alkylCO2A, —(CH2)n-aryl-(CH2)nCO2A, —(CH2)n-heterocycle-(CH2)nCO2A-, or —(CH2)n-cycloalkyl-(CH2)nCO2A, where n is an integer from 0 to about 200, and A is an alkali metal cation;
- with the proviso that only one of R1 and R2 can be —H;
- comprising:
- (a) combining a zerovalent highly reactive zinc species with an ester of an R1,R2 thiophene having at least two stable leaving groups to form a zinc derivative reagent;
- (b) adding a catalyst to polymerize the zinc derivative reagent to provide a polymer;
- and
- (c) adding an alkali metal base to form an alkali metal salt of the polymer.
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A method of forming a water-soluble regioregular polymer having formula I:
- wherein R1 and R2 are independently —H, -alkylCO2A, —(CH2)n-aryl-(CH2)nCO2A, —(CH2)n-heterocycle-(CH2)nCO2A-, or —(CH2)n-cycloalkyl-(CH2)nCO2A, where n is an integer from 0 to about 200, and A is an alkali metal cation;
- with the proviso that only one of R1 and R2 is —H;
- comprising:
- (a) reacting a compound of the formula:
- wherein R1′ and R2′ are independently —H, -alkylCO2ester, —(CH2)n-aryl-(CH2)nCO2ester, —(CH2) n-heterocycle-(CH2)nCO2ester, or —(CH2)n-cycloalkyl-(CH2)nCO2ester, where n is an integer from 0 to about 200, and ester is an alkyl ester, with the proviso that only one of R1′ and R2′ is —H, with a halogen selected from bromine and iodine, to provide a halogenated thiophene;
- (b) reacting a zerovalent highly reactive zinc species with the halogenated thiophene to provide a zinc derivative reagent;
- (c) adding a Ni(II) catalyst to polymerize the zinc derivative reagent to provide a polymer;
- and
- (d) adding an alkali metal base to form an alkali metal salt of the polymer.
6 more elements
Dependencies are inferred from the claim text.