# US 11,028,265 B2 · Electrically conducting poly(pyrazoles)

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- Number: US 11,028,265 B2
- Document ID: US11028265B2
- Status: Granted
- Kind: B2
- Application number: 16/218,446
- Filed: 2018-12-12
- Published: 2019-06-20
- Granted: 2021-06-08
- Earliest claimed: 2017-12-14
- Assignees: The Government of the United States of America, as represented by the Secretary of the Navy
- Applicants: The Government of the United States of America, as represented by the Secretary of the Navy
- Inventors: Brett D. Martin; Ian D. Giles; Jawad Naciri; Paul T. Charles; Scott A. Trammell; Jeffrey R. Deschamps; Jeffrey C. Depriest
- Web page: https://patentgrep.com/patent/US11028265B2

## CPC

- C08L 79/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C07D 231/38: Nitrogen atoms (nitro radicals C07D231/16)
- C08G 73/0616: {with only two nitrogen atoms in the ring}
- C08L 2203/204: use in solar cells
- H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes}
- Y02E 10/549: Organic PV cells
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## 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.

## Claims

### Claim 1

A method of making a poly(3-amino-4-nitropyrazole) comprising the steps of:
adding water to a flask;
adding potassium hydroxide to the water in the flask;
stirring the potassium hydroxide and the water in the flask;
dissolving the potassium hydroxide in the water in the flask and making a first solution;
adding 4-nitro 3-aminopyrazole to the first solution;
heating the 4-nitro 3-aminopyrazole in the first solution;
dissolving the 4-nitro 3-aminopyrazole in the first solution and forming a second solution;
adding sodium or potassium persulfate to the second solution; and
forming an electrically conducting poly(pyrazole);
wherein the electrically conducting poly(pyrazole) comprises poly(3-amino-4-nitropyrazole).

### Claim 2 (depends on 1)

The method of making the poly(3-amino-4-nitropyrazole) of claim 1 wherein the step of dissolving the 4-nitro 3-aminopyrazole in the first solution and forming a second solution was at a temperature of 70° C. and wherein a potassium and a deprotonated nitrogen of the pyrazole ring formed a 1:1 molar complex.

### Claim 3 (depends on 2)

The method of making the poly(3-amino-4-nitropyrazole) of claim 2 wherein the step of adding sodium or potassium persulfate to the second solution gives a final molar ratio of 1.2 moles persulfate to 1.0 moles 4-nitro-3-aminopyrazole.