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 10 2019
Accepted
19 12 2019
First published
20 12 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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