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 nov 2017
Accepted
05 feb 2018
First published
06 feb 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

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