Solution-processable triazole-based polymers and methods of making the same

Patent metadata

Field	Value
Publication number	US-12344688-B2
Application number	US-202017634406-A
Country	US
Kind code	B2
Filing date	Aug 20, 2020
Priority date	Aug 27, 2019
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

Abstract

Disclosed herein are polymers comprising at least one alkyne functional group, at least one azide functional group, and a conformational bend outside of coplanarity of 30 or greater. Also disclosed herein are methods of making and using the same.

First claim

What is claimed is:

1. A polymer, comprising:
at least one azide functional group;
at least one alkyne functional group; and
a spirocenter,
wherein the polymer is obtained from (i) a first monomer having at least a first azide functional group and (ii) a second monomer having at least a first alkyne functional group, and
wherein at least one monomer of the first and second monomers has a conformational bend in which one or more bonds connecting the at least one monomer to one or more additional monomers in a monomer chain are 30 degrees or greater away from co-planarity.

2. The polymer of claim 1 , wherein the polymer has a degree of polymerization of 30 or greater based on the number-average degree of polymerization.

3. The polymer of claim 1 , wherein the polymer has a molecular weight of 60,000 g/mol or greater based on the weight average molecular weights for the polymer.

4. The polymer of claim 1 , wherein the polymer has a polydispersity index of 1 or greater.

5. The polymer of claim 1 , wherein the polymer has a solubility of 20 mg/mL or greater in common organic solvents, and wherein the common organic solvents comprise one or more of acetaldehyde, acetic acid, acetone, acetonitrile, butanediol, butoxyethanol, butyric acid, diethanolamine, diethylenetriamine, dimethyl acetamide (DMAc), dimethylformamide (DMF), dimethoxy ethane, dimethyl sulfoxide (DMSO), dioxane, ethanol, ethylamine, ethylene glycol, formic acid, furfuryl alcohol, glycerol, methanol, methyl diethanolamine, methyl isocyanide, N-methyl-2-pyrrolidone (NMP), propanol, propanediol, propanoic acid, propylene glycol, pyridine, tetrahydrofuran (THF), triethylene glycol, dimethyl hydrazine, hydrazine, hydrofluoric acid, hydrogen peroxide, nitric acid, sulfuric acid, pentane, cyclopentane, hexane, cyclohexane, benzene, toluene, chloroform, diethyl ether, and dichloromethane.

6. The polymer of claim 1 , wherein the polymer further comprises:
monomers comprising:
at least two azide functional groups; and
at least two alkyne functional groups, and

wherein the polymer comprises a polytriazole.

7. The polymer of claim 1 , wherein the polymer comprises two or more spirocenters.

8. The polymer of claim 1 , further comprising one or more of an alkane group, an ester functional group, a halide functional group, a cycloalkane functional group, an aromatic functional group, an amide functional group, a heterocyclic functional group, a thioester functional group, an imide functional group, a carbamate functional group, and a carbonate functional group.

Assignees

• Georgia Tech Res Inst

Inventors

• Bruno Nicholas
• Finn M G

Classifications

• C08F4/26

  of manganese, iron group metals or platinum group metals · CPC title

• C08F2/06

  Organic solvent · CPC title

• C08F26/06 Primary

  by a heterocyclic ring containing nitrogen · CPC title

• C08G73/08 Primary

  Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles · CPC title