Journal
NEW JOURNAL OF CHEMISTRY
Volume 42, Issue 22, Pages 18269-18277Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8nj03510e
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Funding
- National Natural Science Foundation of China [51773076, 21503090]
- Open Project of State Key Laboratory of Supramolecular Structure and Materials [SKLSSM201813]
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New D-pi-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 center dot center dot center dot pi 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.
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