期刊
DYES AND PIGMENTS
卷 137, 期 -, 页码 111-116出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2016.10.004
关键词
Organogel; Non-conventional; Supramolecular self-assembly; Fluorescence; Mechanochromism; Chemosensor
资金
- National Natural Science Foundation of China [21472111, 51373039]
- China Three Gorges University [KJ2014H006]
A fluorescent non-conventional organogelator, 2-(anthracen-9-yl)-4,5-diphenyl-1H-imidazole, was found to be an integrated platform with multiple functionality. Balanced supramolecular interactions, based on pi-pi stacking between aromatic rings and intermolecular hydrogen bonding between neighboring imidazole rings, promote solvent gelation with a critical gelation concentration of 1.2 mg/mL (3.03 x 10(-3) mol/L) in cyclohexane. The intermolecular interactions can be modified by mechanical force, giving it piezochromic properties, and the xerogel has a much higher specific surface area, conferring higher sensitivity to pressure compared to the crystalline powder. The presence of imidazole in the gelator enables a selective response to fluoride anion. Addition of 0.3 equivalents of fluoride anion destroyed the gel (1.2 mg/mL), resulting in precipitation of a red solid that was isolated and identified by H-1 NMR and X-ray single crystal analysis. The red solid can be converted to the starting gelator molecule by addition of water to provide a recyclable chemosensor. This system represents a unique example of a simple organogelator with multiple functionality. (C) 2016 Elsevier Ltd. All rights reserved.
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