Fabrication of a conjugated polymer

Patent metadata

Field	Value
Publication number	US-12258441-B1
Application number	US-202418674496-A
Country	US
Kind code	B1
Filing date	May 24, 2024
Priority date	May 24, 2024
Publication date	Mar 25, 2025
Grant date	Mar 25, 2025

Abstract

A method of fabricating a conjugated polymer may include alkylating a carbazole with an alkyl bromide, in a solvent mixture, to form an alkyl carbazole; brominating the alkyl carbazole to form an N-alkyldibromocarbazole; and reacting the N-alkyldibromocarbazole with a distanyl-biselenophene in the presence of a catalyst to form a conjugated polymer having repeating units of formula (5)

First claim

The invention claimed is:

1. A method of fabricating a conjugated polymer, comprising:
alkylating 9H-carbazole with 1-bromohexane, in a solvent mixture, to form 9-hexyl-9H-carbazole;
brominating the 9-hexyl-9H-carbazole to form an N-hexyldibromocarbazole; and
reacting the N-hexyldibromocarbazole with a distanyl-biselenophene in the presence of a catalyst to form a conjugated polymer having repeating units of formula 5

2. The method of claim 1 , wherein the catalyst is a metal catalyst.

3. The method of claim 1 , wherein the catalyst comprises palladium.

4. The method of claim 1 , wherein the solvent mixture comprises an organic solvent and a strong base.

5. The method of claim 4 , wherein the strong base is KOH.

6. The method of claim 4 , wherein the organic solvent is selected from the group consisting of dimethylsulfoxide (DMSO), dimethylformamide (DMF), acetonitrile, ethanol, and n-methyl-2-pyrrolidone (NMP).

7. The method of claim 4 , wherein the organic solvent is DMSO.

8. The method of claim 1 , wherein the distanyl-biselenophene is 5,5′-bis(trimethylstannyl-2,2′-biselenophene).

9. The method of claim 1 , further comprising:
mixing the N-hexyldibromocarbazole, the distanyl-biselenophene, an organic solvent, and an inorganic salt to form a first mixture;
combining the first mixture with the catalyst and a metal halide to form a second mixture; and
stirring the second mixture to form the conjugated polymer.

10. The method of claim 1 , wherein the inorganic salt is selected from the group consisting of sodium fluoride (NaF), calcium fluoride (CaF), potassium fluoride (KF), lithium fluoride (LiF), and cesium fluoride (CsF).

11. The method of claim 9 , wherein the second mixture is stirred at a temperature of 40 to 80° C. under an inert gas flow for 15 to 21 hours.

12. The method of claim 11 , wherein the inert gas is Ar.

13. The method of claim 9 , wherein the second mixture is stirred at a temperature of 60° C. for 18 hours.

14. The method of claim 9 , wherein the first mixture comprises a molar ratio of the N-hexyldibromocarbazole to the distanyl-biselenophene of 0.5:0.45 to 1.5:0.85.

15. The method of claim 14 , wherein the molar ratio is 1:0.6.

16. The method of claim 9 , wherein the metal halide is copper (I) iodide.

Assignees

• Imam Mohammad Ibn Saud Islamic Univ

Inventors

• Yousef Tarek Ahmed
• Shaaban Saad
• Soliman Ahmed Abdel Nazeer
• Mohamed Mohamed Alaa

Classifications

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C08G61/124 Primary

  with a five-membered ring containing one nitrogen atom in the ring · CPC title

• H01G11/32

  Carbon-based · CPC title

• C08G2261/516

  ion-conductive · CPC title

• C08G2261/3225

  containing one or more Se atoms as the only heteroatom · CPC title