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US 8,513,377 B2Granted
Selenium-based monomers and conjugated polymers, methods of making, and use thereof
AssigneeUniversity of Connecticut
InventorsGregory A. Sotzing, Tanmoy Dey
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Abstract
Substituted selenophene monomers, and polymers and copolymers having units derived from a substituted selenophene are disclosed. Also provided are methods of making and using the same.
Claims21
A polymer, comprising:
- a unit derived from a monomer according to structure (I):
- wherein each instance of Q is O or S;
- each of R1a, R1b, R2a, R2b, R3, and R4 independently is hydrogen;
- C1-C20 alkyl, C1-C20 haloalkyl, aryl, C1-C20 alkoxy, C1-C20 haloalkoxy, aryloxy, —C1-C10 alkyl-O—C1-C10 alkyl, —C1-C10 alkyl-O-aryl, —C1-C10 alkyl-aryl;
- or hydroxyl;
- with the proviso that at least one of R1a, R1b, R2a, R2b, R3, and R4 is not hydrogen, and when R1a, R1b, R2a, and R2b are all hydrogen, then at least one of R3 and R4 is other than hydrogen, C1-C20 alkyl, or —C1-C10 alkyl-aryl;
- wherein the C1-C20 alkyl, C1-C20 haloalkyl, aryl, C1-C20 alkoxy, C1-C20 haloalkoxy, aryloxy, —C1-C10alkyl-O—C1-C10 alkyl, —C1-C10 alkyl-O-aryl, —C1-C10 alkyl-aryl group each may be optionally substituted with one or more of C1-C20 alkyl;
- aryl;
- halogen;
- hydroxyl;
- —N—(R7)2 wherein each R7 is independently hydrogen or C1-C6 alkyl;
- cyano;
- nitro;
- —COOH;
- —S(═O)C0-C10 alkyl;
- or —S(═O)2C0-C10 alkyl.
13 more elements
A method, comprising:
- polymerizing a composition by electrochemical or chemical reaction to form a polymer, wherein the composition comprises a monomer according to the structure (I) or (Ia):
- wherein each instance of Q is O or S;
- each of R1a, R1b, R2a, R2b, R3, and R4 independently is hydrogen;
- C1-C20 alkyl, C1-C20 haloalkyl, aryl, C1-C20 alkoxy, C1-C20 haloalkoxy, aryloxy, —C1-C10 alkyl-O—C1-C10 alkyl, —C1-C10 alkyl-O-aryl, —C1-C10 alkyl-aryl;
- or hydroxyl;
- with the proviso that at least one of R1a, R1b, R2aR2b, R3, and R4 is not hydrogen, and when R1a, R1b, R2b are all hydrogen, then at least one of R3 and R4 is other than hydrogen, C1-C20 alkyl, or —C1-C10 alkyl-aryl;
- wherein the C1-C20 alkyl, C1-C20 haloalkyl, aryl, C1-C20 alkoxy, C1-C20 haloalkoxy, aryloxy, —C1-C10alkyl-O—C1-C10 alkyl, —C1-C10 alkyl-O-aryl, —C1C10alkyl-aryl group each may be optionally substituted with one or more of C1-C20 alkyl;
- aryl;
- halogen;
- hydroxyl;
- —N—(R7)2 wherein each R7 is independently hydrogen or C1-C6 alkyl;
- cyano;
- nitro;
- —COOH;
- —S(═O)C0-C10 alkyl;
- or —S(═O)2C0-C10 alkyl;
- and
- X is chloro, bromo, or iodo.
15 more elements
Dependencies are inferred from the claim text.