Method of producing benzo[1,2-B:4,5-B′]dithiophene and benzothiadiazole-based molecular complexes

US9908857B2 · kind B2 · utility

Assignee

• Phillips 66 Company · US

Inventors

• Hualong Pan · Skokie, US
• Kathy Woody · Bartlesville, US
• Brian Worfolk · Bartlesville, US
• Taeshik Earmme · Seattle, US

Key dates

• Filing date: Jul 7, 2017
• Grant date: Mar 6, 2018
• Expiry date: Jul 7, 2037

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P70/50
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A method of forming a molecular complex. The method proceeds by reacting 5-chloro-2,1,3-benzothiadiazole with N-bromosuccinimide to produce 4,7-dibromo-5-chlorobenzo[c][1,2,5]thiadiazole. 4,7-dibromo-5-chlorobenzo[c][1,2,5]thiadiazole is then reacted with trimethyl[4-(2-octyldodecyl)thiophen-2-yl]stannane to produce 5-chloro-4,7-bis(4-(2-octyldodecyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole. 4, 7-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-5-chlorobenzo[c][1,2,5]thiadiazole is subsequently synthesized from 5-chloro-4,7-bis(4-(2-octyldodecyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole. 4,7-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-5-chlorobenzo[c][1,2,5]thiadiazole with tributyl(thiophen-2-yl)stannane is then reacted to produce 4-bromo-5,6-difluoro-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole. This is followed by reacting 4,7-dibromo-5-chloro-2,1,3-benzothiadiazole with tributyl(thiophen-2-yl)stannane to produce 4-bromo-5-chloro-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole. trimethyl[4-(2-octyldodecyl)thiophen-2-yl]stannane is then reacted with and 4-bromo-5-chloro-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole to produce 5-chloro-4-(4-(2-octyldodecyl)thiophen-2-yl)-7-(thiophen-2-yl)ben…