Electrically conducting poly(pyrazoles)

Inventors

Martin, Brett D. • Giles, Ian D. • Naciri, Jawad • Charles, Paul T. • Trammell, Scott A. • Deschamps, Jeffrey R. • DePriest, Jeffrey C.

Assignees

US Department of Navy

Abstract

This disclosure concerns electrically conducting poly(pyrazoles). The concept of oligomerizing and polymerizing substituted aminopyrazole derivatives combined with a monomer activation procedure involving base-mediated conversion of the protonated pyrazole ring nitrogen to amine salt was developed. This disclosure concerns the specific chemistries needed for the synthesis of a pyrazole monomer used in the polymer synthesis. The procedure used for blending the novel polypyrazoles with other compounds needed for construction of solar cells for testing was developed. This disclosure concerns the concept of using these types of heteroatom-rich, electron-deficient oligomers or polymers as n-dopable or p-dopable electron acceptors in photovoltaic cells. This disclosure concerns synthesizing the starting monomer compounds and polypyrazoles.

Core Innovation

This invention discloses electrically conducting poly(pyrazoles) synthesized by oligomerizing and polymerizing substituted aminopyrazole derivatives combined with a monomer activation procedure involving base-mediated conversion of the protonated pyrazole ring nitrogen to amine salt. Specific chemistries for synthesizing pyrazole monomers used in polymer synthesis were developed, as well as procedures for blending the novel polypyrazoles with other compounds for constructing solar cells.

The disclosed poly(pyrazoles) are heteroatom-rich, electron-deficient oligomers or polymers that can serve as n-dopable or p-dopable electron acceptors in photovoltaic cells. This chemistry enables synthesis of starting monomer compounds and polypyrazoles with high electron transport rates, versatile redox behavior, and simple one-step synthesis from low-cost starting materials, facilitating the production and investigation of derivatives.

The problem addressed is the high cost and limited efficiency of existing polymer-based solar cells and expensive synthesis of polymers used therein. Silicon-based solar cells, though efficient, are costly to manufacture. The invention aims to provide polypyrazoles that increase solar cell efficiency while costing significantly less to synthesize, with starting materials priced approximately at $2.00 per gram in bulk, and yielding photocells with substantially higher photocurrent responsivity compared to existing polymers.

Claims Coverage

There are two independent claims focusing on a specific poly(3-aminopyrazole-4-carbonitrile) compound and a method of making it.

The claims cover the specific polymeric compound poly(3-aminopyrazole-4-carbonitrile) and a detailed synthesis method using base-mediated monomer activation and controlled oxidation to form a conducting polymer of defined oligomer length.

Stated Advantages

Documented Applications