# US 7,608,179 B1 · Bis(thienyl)isopyrazoles and process for preparing and method for using bis(thienyl)isopyrazoles

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- Number: US 7,608,179 B1
- Document ID: US7608179B1
- Status: Granted
- Kind: B1
- Application number: 12/178,947
- Filed: 2008-07-24
- Granted: 2009-10-27
- Earliest claimed: 2006-11-25
- Assignees: The United States of America as represented by the Secretary of the Navy
- Inventors: David J. Irvin; David L. Witker; John D. Stenger-Smith; Jennifer A. Irvin
- Web page: https://patentgrep.com/patent/US7608179B1

## CPC

- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 333/22: Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention demonstrates the synthesis of a new pyrazole-containing monomer by an easily implemented two-step process. This monomer can be electropolymerized to yield a stable n-doping polymer that may easily be electrochemically characterized. It is demonstrated that the electrochemical behavior of the polymer films produced is dependent upon the conditions applied during electrodeposition. Films deposited by cycling only at relatively positive potentials (0 to 2000 mV) show less intense n-doping responses than those films obtained by scanning the applied potential throughout a wider range (−2000 mV to 2000 mV).

## Claims

### Claim 1

A process for preparing a stable n-doping conjugated electroactive polymer comprising:
providing a solution containing monomeric 3,5-Dithien-2-yl-4,4-dimethylpyrazole in tetramethylammonium tetrafluoroborate and acetonitrile;
contacting a platinum substrate with said solution;
selecting a first electrical potential necessary to oxidize 3,5-Dithien-2-yl-4,4-dimethylpyrazole and a second electrical potential necessary to reduce 3,5-Dithien-2-yl-4,4-dimethylpyrazole;
applying an electrical potential to said platinum substrate in contact with said solution;
cycling said electrical potential at a predetermined rate of change between said selected first electrical potential and said selected second electrical potential to effect electrodeposition of poly(3,5-Dithien-2-yl-4,4-dimethylpyrazole) on said platinum substrate and;
growing a film of stable n-doping poly(3,5-Dithien-2-yl-4,4-dimethylpyrazole) of a desired thickness on said platinum substrate by cycling said electrical potential for a predetermined time.

### Claim 2 (depends on 1)

The process of claim 1 wherein said selected first electrical potential and said selected second electrical potential are about +2000 mV and −2000 mV, respectively, with respect to a neutral reference.