Synthesis, structure, and aggregation-induced emission of a novel lambda (Λ)-shaped pyridinium salt based on Troger's base
Synthesis, structure, and aggregation-induced emission of a novel lambda (Λ)-shaped pyridinium salt based on Troger's base
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DOI：
10.1021/jp0711601
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发表时间：
2007-08-30
影响因子：
3.7
通讯作者：
Jiang, Min-Hua
中科院分区：
文献类型：
--
作者：
Yuan, Chun-Xue;Tao, Xu-Tang;Jiang, Min-Hua
设计、合成并表征了一种基于 Troger 碱的新型 Lambda 型吡啶鎓盐 2,8-(6H,12H-5,11-亚甲基二苯并[b,f]重氮亚萘基)-二(对乙烯基-N-甲基-吡啶鎓)二甲苯磺酸盐(简称 DMDPS)。 DMDPS 表现出典型的聚集诱导发射 (AIE) 行为，在溶液中几乎不发光，但在固态下高度发光。分析比较了DMDPS与1,4-苯基-二(对乙烯基-N-甲基-吡啶鎓)二甲苯磺酸盐(简称DPPS)的结构和光学性质的差异。结论是，扭曲的分子构型引起的松散堆积可以减少距离依赖性分子间猝灭效应，从而在聚集状态下产生强烈的荧光，而引起非辐射失活过程的对映异构化和/或分子内振动运动可以导致溶液中的荧光猝灭。作为一种水溶性AIE活性材料，DMDPS在光学和生物研究领域具有潜在的应用前景。
A novel Lambda-shaped pyridinium salt 2,8-(6H,12H-5,11-methanodibenzo[b,f]diazocineylene)-di(p-ethenyl-N-methyl-pyridinium) ditosylate (abbreviated as DMDPS) based on Troger's base was designed, synthesized and characterized. DMDPS exhibits a typical aggregation-induced emission (AIE) behavior that is virtually nonemissive in solution but highly luminescent in solid state. The difference between the structure and the optical properties of DMDPS and 1,4-phenyl-di(p-ethenyl-N-methyl-pyridinium) ditosylate (abbreviated as DPPS) are analyzed and compared. It is concluded that the loose stacking caused by twisted molecular configuration could reduce the distance-dependent intermolecular quenching effect to produce intense fluorescence in the aggregation state while the enantiomerization and/or the intramolecular vibrational motion which induce the nonradiative deactivation process could cause fluorescence quenching in the solution. As a water-soluble AIE-active material, DMDPS would have potential application in the area of optical and biological research.