IP Library Granted Patent US 8,907,015
Granted Patent B2
US 8,907,015 · App. 13/133,936 · Granted Dec 9, 2014

Copolymer of pyrene and pyrrole and method of producing the copolymer

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Quick Facts
Patent No.
US 8,907,015
App. No.
13/133,936
Granted
Dec 9, 2014
Kind
B2
Abstract

The present application provides a copolymer including one or more units of pyrene and one or more units of pyrrole. The present application also provides a method of producing a copolymer, including incubating pyrene monomer and pyrrole monomer with an oxidant in the presence of a reaction solvent. Uses of the copolymers are also provided.

Claims (32)

1. A copolymer comprising one or more units of pyrene and one or more units of pyrrole, wherein at least one of the one or more units of pyrene and at least one of the one or more units of pyrrole are bonded together via

linkages in the copolymer.

2. The copolymer of claim 1 , wherein the molar ratio of pyrene to pyrrole in the copolymer is from 99:1 to 30:70.

3. The copolymer of claim 2 , wherein the molar ratio of pyrene to pyrrole in the copolymer is 80:20 to 50:50.

4. The copolymer of claim 1 , wherein pyrene and pyrrole are distributed randomly on the copolymer.

5. The copolymer of claim 1 , wherein the copolymer has the following structure:

wherein:

-Pyrene-Pyrrole- is selected from the group consisting of

each A is independently selected from the group consisting of: nothing,

each B is independently selected from the group consisting of: nothing,

n is any integer from 1 to 40;

R 1 is selected from the group consisting of: H,

R 2 is selected from the group consisting of: H,

6. The copolymer of claim 5 , wherein the copolymer is selected from the group consisting of:

7. The copolymer of claim 1 , wherein the copolymer is linear.

8. The copolymer of claim 1 , wherein the copolymer is branched.

9. The copolymer of claim 1 , wherein the copolymer has a weight average molecular weight of about 500 Da to 10000 Da.

10. The copolymer of any of claim 1 , wherein the copolymer has a thermal decomposition temperature between 400° C. and 800° C.

11. The copolymer of claim 1 , wherein the copolymer has an electrical conductivity between 10 2 and 10 −11 S cm −1 .

12. The copolymer of claim 1 , wherein the copolymer has char yield at 1000° C. between 70% and 95%.

13. The copolymer of claim 1 , wherein 5% to 100% of the copolymer is soluble in organic solvent.

14. The copolymer of claim 13 , wherein the organic solvent is selected from the group consisting of N-methylpyrrolidone (NMP), tetrahydrofuran (THF), chloroform, dimethylformamide (DMF), and dimethylsulfoxide (DMSO).

15. The copolymer of claim 1 , wherein the copolymer has UV absorbance peaks at wavelengths ranging from 250 nm to 800 nm.

16. The copolymer of claim 1 , wherein the copolymer has fluorescence emission peaks at wavelengths ranging from 400 nm to 700 nm.

17. A method of producing a copolymer comprising one or more units of pyrene and one or more units of pyrrole, comprising incubating pyrene monomers and pyrrole monomers with an oxidant in the presence of a reaction solvent, wherein at least one of the one or more units of pyrene and at least one of the one or more units of pyrrole are bonded together via

linkages in the copolymer.

18. The method of claim 17 , wherein the oxidant is selected from the group consisting of FeCl 3 , FeBr 3 , AlCl 3 , AlBr 3 , AlI 3 , CuCl 2 , CuBr 2 , MoCl 5 , SnCl 4 , SnBr 4 , SnI 4 , MgCl 2 , MgBr 2 , MgI 2 , CaCl 2 , CaBr 2 , CaI e , ZnCl 2 , ZnBr 2 , ZnI 2 , BF 3 , TiCl 4 , TiBr 4 , SbCl 5 , and any combination thereof.

19. The method of claim 18 , wherein the oxidant is FeCl 3 .

20. The method of claim 17 , wherein the reaction solvent is selected from the group consisting of nitroalkanes, aromatic nitro compounds, hydrocarbons, halogenated hydrocarbons, nitriles, and any combination thereof.

21. The method of claim 17 , wherein the molar ratio of the oxidant to the total amount of monomers is from 1:1 to 9:1.

22. The method of claim 17 , wherein the incubation temperature is from 10° C. to 100° C.

23. The method of claim 17 , wherein the incubation time is from 1 to 48 hours.

Assignments (4)
RELEASE OF SECURITY INTEREST IN PATENTS, RECORDED ON JANUARY 29, 2019 AT REEL 048373 FRAME 0217 Recorded Sep 22, 2025
From: CRESTLINE DIRECT FINANCE, L.P., AS COLLATERAL AGENT
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 072936/0464 →
RELEASE OF SECURITY INTEREST Recorded Jul 31, 2019
From: CRESTLINE DIRECT FINANCE, L.P.
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 049924/0794 →
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2011
From: LI, XIN-GUI; HUANG, MEI-RONG; HOU, ZHENZHONG
To: TONGJI UNIVERSITY
Reel/Frame 026437/0012 →