Issue 10, 2022

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
05 Feb 2022
Accepted
04 Mar 2022
First published
21 Apr 2022

Org. Chem. Front., 2022,9, 2821-2829

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

C. Tu, K. Lee, J. Chen, C. Chiang, S. Hsu, M. Hsu and C. Liu, Org. Chem. Front., 2022, 9, 2821 DOI: 10.1039/D2QO00187J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements