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Issue 8, 2018
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Syntheses and structures of [7]helicene and double helicene based on dithieno[2,3-b:2′,3′-d]thiophene

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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

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Publication details

The article was received on 23 Nov 2017, accepted on 05 Feb 2018 and first published on 06 Feb 2018


Article type: Research Article
DOI: 10.1039/C7QO01049D
Citation: Org. Chem. Front., 2018,5, 1257-1261
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    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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