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H-bonding and C-H···π assisted mechanofluorochromism of triphenylamine-containing vinylheterocycles bearing cyano and methyl

Abstract

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

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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, Accepted Manuscript
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    H-bonding and C-H···π assisted mechanofluorochromism of triphenylamine-containing vinylheterocycles bearing cyano and methyl

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

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