Pd-Free synthesis of dithienothiophene-based oligoaryls for effective hole-transporting materials by optimized Cu-catalyzed annulation and direct C–H arylation

Dithienothiophene (DTT), a versatile building block for π-conjugated organic materials, has been efficiently synthesized through copper-catalysis with an inexpensive sulfur source in the essential ring-closure/C–S bond formation step, instead of using previously often reported n-butyllithium, costly...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (10), p.2821-2829
Main Authors: Chen-Hsin, Tu, Kun-Mu, Lee, Jui-Heng, Chen, Chia-Hua Chiang, Shen-Chieh Hsu, Ming-Wei, Hsu, Ching-Yuan, Liu
Format: Article
Language:English
Subjects:
Butyllithium
Catalysis
Chemical reactions
Chemical synthesis
Copper
Couplings
Dithiothreitol
Energy conversion
Energy conversion efficiency
Organic chemistry
Organic materials
Palladium
Perovskites
Photovoltaic cells
Solar cells
Solar energy
Sulfur
Transportation
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Summary:Dithienothiophene (DTT), a versatile building block for π-conjugated organic materials, has been efficiently synthesized through copper-catalysis with an inexpensive sulfur source in the essential ring-closure/C–S bond formation step, instead of using previously often reported n-butyllithium, costly bis(phenylsulfonyl)sulfide, or palladium-based catalysis. Furthermore, π-extension from DTT was also achieved step-economically by optimized copper-catalyzed direct C–H arylation reactions, giving three new oligoaryls that were used as effective hole-transporting materials (HTMs) in perovskite solar cells. One of the solar devices demonstrated the highest energy conversion efficiency of 14.67%. For the first time, [Cu]-catalyzed direct C–H/C–I couplings were used as key transformations to access small molecular HTMs.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00187j