Electrically conducting poly(pyrazoles)

Patent metadata

Field	Value
Publication number	US-11028265-B2
Application number	US-201816218446-A
Country	US
Kind code	B2
Filing date	Dec 12, 2018
Priority date	Dec 14, 2017
Publication date	Jun 8, 2021
Grant date	Jun 8, 2021

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.

First claim

What we claim is:

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).

2. 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.

3. 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.

Assignees

• Us Gov Sec Navy

Inventors

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

Classifications

• C07D231/38 Primary

  Nitrogen atoms (nitro radicals C07D231/16) · CPC title

• C08L2203/204

  use in solar cells · CPC title

• C08L79/04 Primary

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/0616

  with only two nitrogen atoms in the ring · CPC title

• H01B1/127

  comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes · CPC title