Issue 6, 2020

Trisulfur radical anion-triggered stitching thienannulation: rapid access to largely π-extended thienoacenes

Abstract

Largely π-extended rylene diimide-fused thienoacenes, a new family of fully fused electron donor–acceptor (D–A) molecules, have been readily synthesized by a novel trisulfur radical anion (S3˙)-triggered stitching thienannulation strategy. The ladder-type fused thiophene cores are constructed in a stitching manner through multiple carbon–sulfur bond formation between acetylenic rylene dyes and S3˙. A detailed mechanistic study of these stitching thienannulations unveiled the multiple reactivities of S3˙. Physical properties of the newly formed D–A, A–D–A, and D–A–D type thienoacenes have also been investigated, which revealed their precisely controllable electronic properties.

Graphical abstract: Trisulfur radical anion-triggered stitching thienannulation: rapid access to largely π-extended thienoacenes

Supplementary files

Article information

Article type
Edge Article
Submitted
22 Okt. 2019
Accepted
19 Dec. 2019
First published
20 Dec. 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 1503-1509

Trisulfur radical anion-triggered stitching thienannulation: rapid access to largely π-extended thienoacenes

F. Su, S. Chen, X. Mo, K. Wu, J. Wu, W. Lin, Z. Lin, J. Lin, H. Zhang and T. Wen, Chem. Sci., 2020, 11, 1503 DOI: 10.1039/C9SC05332H

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