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D–π–A azine based AIEgen with solvent dependent response towards a nerve agent
RSC Advances ( IF 3.9 ) Pub Date : 2020-7-8 , DOI: 10.1039/d0ra04941g
Munusamy Sathiyaraj 1 , Viruthachalam Thiagarajan 1, 2
Affiliation  

We developed a D–π–A based unsymmetrical azine molecule 4-((E)-((E)-(4-(dipropylamino)benzylidene)hydrazono)methyl)benzonitrile [DPBN] and studied its optical and aggregation induced emission properties. The DPBN molecule shows good aggregation induced emission (AIE) behaviour with 1157-fold fluorescence enhancement in the aggregated state. In addition to that, both colorimetric as well as fluorometric sensing studies revealed that DPBN selectively detects diethylchlorophosphate (DCP), a potent nerve agent. Interestingly, DPBN shows solvent dependent optical output in the presence of DCP via two different mechanisms. In the monomer state, it shows red shifted fluorescence enhancement along with color change from colorless to orange color via the formation of a new intramolecular charge transfer state in pure tetrahydrofuran (THF). In the aggregated state, DPBN shows blue shifted emission with fluorescence enhancement in THF–water mixture by protonation at the amine nitrogen centre. Thus, DPBN can be used as a diagnostic measure to selectively detect nerve agents like DCP. This study also paves the way for further development of molecular probes for nerve agents that would represent immense implications in various fields of chemistry and biology.

中文翻译:

基于 D–π–A 吖嗪的 AIEgen,对神经毒剂具有溶剂依赖性反应

我们开发了一种基于D-π-A的不对称吖嗪分子4-(( E )-(( E )-(4-(二丙氨基)亚苯亚甲基)亚肼基)甲基)苯甲腈[ DPBN ],并研究了其光学和聚集诱导发射特性。DPBN分子表现出良好的聚集诱导发射 (AIE) 行为,聚集状态下荧光增强 1157 倍。除此之外,比色和荧光传感研究表明DPBN选择性检测二乙基氯磷酸盐 ( DCP ),一种强效神经毒剂。有趣的是,DPBN在DCP 存在的情况下通过两种不同的机制显示出与溶剂相关的光学输出。在单体状态下,它通过在纯四氢呋喃 (THF) 中形成新的分子内电荷转移态,显示出红移荧光增强以及颜色从无色变为橙色的变化。在聚集状态下,DPBN通过胺氮中心的质子化在 THF-水混合物中显示出蓝移发射和荧光增强。因此,DPBN可用作诊断措施来选择性检测DCP等神经毒剂。这项研究还为神经毒剂分子探针的进一步开发铺平了道路,这将在化学和生物学的各个领域产生巨大的影响。
更新日期:2020-07-08
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