A fluorescent non-conventional organogelator with gelation-assisted piezochromic and fluoride-sensing properties

作者：Li, Ruohan; Wang, Sa; Li, Qian; Lan, Haichuang; Xiao, Shuzhang^*; Li, Yaqian; Tan, Ronghua; Yi, Tao^*

来源：Dyes and Pigments, 2017, 137: 111-116.

DOI：10.1016/j.dyepig.2016.10.004

• Organogel
• Non-conventional
• Supramolecular self-assembly
• Fluorescence
• Mechanochromism
• Chemosensor

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.

• 出版日期2017-2
• 单位三峡大学; 复旦大学