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Synthesis and properties of [7]helicene and [7]helicene-like compounds with a cyclopenta[1,2-b:4,3-b′]dithiophene or dithieno[2,3-b:3′,2′-d]heterole skeleton

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Abstract

A series of [7]helicene and [7]helicene-like compounds composed of a cyclopenta[1,2-b:4,3-b′]dithiophene or dithieno[2,3-b:3′,2′-d]heterole moiety and two naphthalene moieties were successfully synthesized from a common synthetic intermediate, 1,1′-binaphtho[2,1-b]thiophene. Their helical structures were confirmed by X-ray crystallographic analysis. The photophysical properties of them and their benzene analogues were investigated via absorption and fluorescence spectroscopy and theoretical calculations to correlate the effect of the five-membered rings in their π-conjugated skeleton. Through these investigations, the photophysical properties were found to largely depend on a combination of the central five-membered ring and the neighboring two aromatic rings. In particular, a combination of the central five-membered ring with electron-withdrawing character and the two neighboring thiophene rings was revealed to induce red-shifted emission.

Graphical abstract: Synthesis and properties of [7]helicene and [7]helicene-like compounds with a cyclopenta[1,2-b:4,3-b′]dithiophene or dithieno[2,3-b:3′,2′-d]heterole skeleton

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Publication details

The article was received on 15 Sep 2017, accepted on 07 Nov 2017 and first published on 16 Nov 2017


Article type: Paper
DOI: 10.1039/C7CP06342C
Citation: Phys. Chem. Chem. Phys., 2018, Advance Article
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    Synthesis and properties of [7]helicene and [7]helicene-like compounds with a cyclopenta[1,2-b:4,3-b′]dithiophene or dithieno[2,3-b:3′,2′-d]heterole skeleton

    K. Uematsu, K. Noguchi and K. Nakano, Phys. Chem. Chem. Phys., 2018, Advance Article , DOI: 10.1039/C7CP06342C

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