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Solvent‐assisted planar structure of a stilbene‐based salicylhydrazone compound: crystal structure, solvent‐ and aggregation‐induced emission, and switchable luminescence colouration
Author(s) -
Fang Zong-Bin,
Zhang Bin,
Yang Qi-Zheng,
Zheng Wenxu,
Hu Xiao-Lin,
Huang Xi-He,
Huang Chang-Cang,
Zhuang Nai-Feng,
Wu Shu-Ting
Publication year - 2020
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229620008037
Subject(s) - luminescence , monoclinic crystal system , molecule , solvent , dimethyl sulfoxide , crystallography , crystal structure , chemistry , hydrogen bond , dihedral angle , stacking , sulfoxide , photochemistry , materials science , organic chemistry , optoelectronics
A novel stilbene‐based salicylhydrazone compound {systematic name: ( E )‐4,4′‐(ethene‐1,2‐diyl)bis[( N ′ E )‐ N ′‐(2‐hydroxybenzylidene)benzohydrazide] dimethyl sulfoxide disolvate, C 30 H 24 N 4 O 4 ·2C 2 H 6 OS or L ·2DMSO} was synthesized and characterized by single‐crystal X‐ray diffraction, powder X‐ray diffraction and luminescence spectroscopy. The title compound crystallizes in the monoclinic space group P 2 1 / c , with half a symmetry‐independent L molecule and one dimethyl sulfoxide (DMSO) solvent molecule in the asymmetric unit. The L molecule adopts an almost planar structure, with a small dihedral angle between the planes of the stilbene and salicylhydrazone groups. There are multiple π–π stacking interactions between adjacent L molecules. The DMSO solvent molecules act as proton donors and acceptors, forming hydrogen bonds of various strengths with the L molecules. In addition, the geometry optimization of a single molecule of L and its luminescence properties either in solution, as a solvated solid or as a desolvated solid were studied. The compound shows an aggregation‐induced emission (AIE) effect and exhibits switchable luminescence colouration in the solid state by the simple removal or re‐addition of the DMSO solvent.