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Issue 22, 2018
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H-Bonding and C–H⋯π assisted mechanofluorochromism of triphenylamine-containing vinylheterocycles bearing cyano and methyl groups

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Abstract

New D–π–A-type triphenylamine-containing benzimidazoles, benzoxazoles and benzothiazoles have been synthesized. It was found that the introduction of a cyano group in vinyl and methyl in triphenylamine was favorable for producing mechanofluorochromism of the fused heterocyclic derivatives. The single crystal X-ray diffraction data revealed that the intermolecular interactions of the H-bonding formed from the cyano group and the C–H⋯π interaction formed from the methyl group would rigidify the molecular conformations, leading to strong solid-state emission. Interestingly, the solid-state emission of the synthesized triphenylamine-containing fused heterocycles bearing cyano and/or methyl groups could be tuned by external mechanical forces on account of the transition between crystalline and amorphous states or between a highly ordered crystalline state and a less ordered state.

Graphical abstract: H-Bonding and C–H⋯π assisted mechanofluorochromism of triphenylamine-containing vinylheterocycles bearing cyano and methyl groups

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Publication details

The article was received on 14 Jul 2018, accepted on 07 Oct 2018 and first published on 08 Oct 2018


Article type: Paper
DOI: 10.1039/C8NJ03510E
Citation: New J. Chem., 2018,42, 18269-18277
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    H-Bonding and C–H⋯π assisted mechanofluorochromism of triphenylamine-containing vinylheterocycles bearing cyano and methyl groups

    J. Peng, J. Zhao, L. Zheng, K. Ye, J. Sun and R. Lu, New J. Chem., 2018, 42, 18269
    DOI: 10.1039/C8NJ03510E

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