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Issue 6, 2017
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Synthesis of bright red-emissive dicyanoetheno-bridged hexa-peri-hexabenzocoronene dimers

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Abstract

The introduction of a dicyanomethyl anion group to hexa-peri-hexabenzocoronene (HBC) substantially enhanced the emission properties of HBC due to a large perturbation of its electronic structure. In addition, dicyanoetheno-bridged HBC dimers obtained from oxidation of a dicyanomethyl HBC anion exhibited bright red emission in solution and solid states. Intramolecular charge transfer interactions between the HBC units and the dicyanoethene bridge induced solvatochromic behaviour in their emission spectra. Dicyanoetheno-bridged HBC dimers exhibited cistrans photoisomerization behaviour in the solution, affording the mixture in cis-isomer dominance in the photostationary state. Theoretical calculations revealed that the cis-isomer is more thermodynamically stable than the trans-isomer.

Graphical abstract: Synthesis of bright red-emissive dicyanoetheno-bridged hexa-peri-hexabenzocoronene dimers

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Publication details

The article was received on 20 Dec 2016, accepted on 11 Jan 2017 and first published on 11 Jan 2017


Article type: Paper
DOI: 10.1039/C6OB02775J
Citation: Org. Biomol. Chem., 2017,15, 1426-1434
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    Synthesis of bright red-emissive dicyanoetheno-bridged hexa-peri-hexabenzocoronene dimers

    K. Oda, S. Hiroto, I. Hisaki and H. Shinokubo, Org. Biomol. Chem., 2017, 15, 1426
    DOI: 10.1039/C6OB02775J

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