Issue 8, 2018

Syntheses and structures of [7]helicene and double helicene based on dithieno[2,3-b:2′,3′-d]thiophene

Abstract

Based on dithieno[2,3-b:2′,3′-d]thiophene, three novel helicenes including helicene (rac-1), double helicene (rac-2), and benzohexathia[7]helicene (rac-3), and one bull's horn-shaped benzohexathienoacene (4) have been synthesized and reported in this paper. In the helicenes, the sulfur atoms of terminal thiophenes are inside the helical structures. X-ray crystallographic analysis exhibited the helical configuration of rac-1 and the bull's horn-shaped configuration of 4. Multiple types of intermolecular interactions, including S⋯S, C⋯C and π⋯π interactions, were observed between the adjacent molecules in the crystals of rac-1 and 4. In addition, a remarkable bathochromic shift was found in the absorption behaviors for rac-3 and 4 compared to rac-1; the integrated absorbance in rac-2 is approximately twice that of rac-1.

Graphical abstract: Syntheses and structures of [7]helicene and double helicene based on dithieno[2,3-b:2′,3′-d]thiophene

Supplementary files

Article information

Article type
Research Article
Submitted
23 ⵏⵓⵡ 2017
Accepted
05 ⴱⵕⴰ 2018
First published
06 ⴱⵕⴰ 2018

Org. Chem. Front., 2018,5, 1257-1261

Syntheses and structures of [7]helicene and double helicene based on dithieno[2,3-b:2′,3′-d]thiophene

X. Liu, H. Sun, W. Xu, S. Wan, J. Shi, C. Li and H. Wang, Org. Chem. Front., 2018, 5, 1257 DOI: 10.1039/C7QO01049D

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