Aggregation-Induced Fluorescence Behavior of Triphenylamine-Based Schiff Bases: The Combined Effect of Multiple Forces

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• 作者：Mingdi Yang ; Dongling Xu ; Wengang Xi ; Lianke Wang ; Jun Zheng ; Jing Huang ; Jingyan Zhang ; Hongping Zhou ; Jieying Wu ; Yupeng Tian
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：October 18, 2013
• 年：2013
• 卷：78
• 期：20
• 页码：10344-10359
• 全文大小：1291K
• 年卷期：v.78,no.20(October 18, 2013)
• ISSN：1520-6904

文摘

Eight triphenylamine (TPA)-based Schiff bases that exhibit different aggregation-induced emission (AIE) or aggregation-caused quenching (ACQ) behavior in tetrahydrofuran (THF)/water mixtures have been synthesized and characterized. The photophysical properties in solution, aqueous suspension, film, and the crystalline state along with their relationships were comparatively investigated. The single-crystal structures of 1鈥?b>8 indicate that compact 蟺路路路蟺 stacking or excimers induce fluorescence quenching of 1, 2, 5, and 7. However, the existence of J aggregates or multiple intra- and intermolecular interactions restrict the intramolecular vibration and rotation, enabling compounds 3, 4, 6, and 8 to exhibit good AIE character. The size and growth process of particles with different water fractions were studied using scanning electron microscopy, which demonstrated that smaller uniformly dispersed nanoparticles in the THF/water mixtures favor fluorescence emission. The above results suggest that the combined effects of multiple forces caused by structural variation have a great influence on their molecular packing, electronic structure, and aggregation-induced fluorescence properties. In addition, piezofluorochromic experiments verified the potential applications of 4 and 6.