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Rationally Designed Furocarbazoles as Multifunctional Aggregation Induced Emissive Luminogens for the Sensing of Trinitrophenol (TNP) and Cell Imaging
ChemPhotoChem ( IF 3.7 ) Pub Date : 2020-05-12 , DOI: 10.1002/cptc.202000090
Valmik P. Jejurkar 1 , Gauravi Yashwantrao 1 , B. Pradeep K. Reddy 2 , Anuja P. Ware 3 , Subhash S. Pingale 3 , Rohit Srivastava 2 , Satyajit Saha 1
Affiliation  

Two structurally unique aggregation induced emission (AIE)‐active luminogens have been designed and synthesized based on the furocarbazole skeleton. Such small molecule AIEgens were designed based on forbidden planarity and engineering a twist into the scaffold to realize induction of emission in the aggregated states. The structures were fully characterized and their thermal stabilities, electronic properties, photophysical and electrochemical properties were systematically investigated. The unique twist in the molecules as evident from their X‐ray crystal structure along with the short intermolecular interactions enhances the structural rigidification and restricts detrimental π–π stacking interactions, restricting the internal rotations (RIR) accompanied by a curb of the ICT process, resulting in enhanced emission in the aggregated state. This intriguing luminescent property enabled one of the luminogens to selectively detect trinitrophenol (TNP) over other nitroaromatics in both aqueous and organic media at nanomolar concentrations. Moreover, the good photostabilities and biocompatibilities empowered both luminogens to function as fluorescent bioprobes for cancer cell imaging.

中文翻译:

合理设计的呋喃咔唑作为三聚酚(TNP)和细胞成像传感的多功能聚集诱导的发光源。

基于呋喃咔唑骨架,已经设计并合成了两种结构独特的聚集诱导发射(AIE)活性发光剂。此类小分子AIEgens是基于禁止的平面性设计的,并设计了一个扭曲进入支架的结构,以实现聚集态发射的诱导。对该结构进行了充分表征,并对其热稳定性,电子性质,光物理和电化学性质进行了系统研究。从分子的X射线晶体结构以及较短的分子间相互作用可以看出,分子的独特扭曲增强了结构的刚性,并限制了有害的π-π堆积相互作用,从而限制了内部旋转(RIR)并限制了ICT过程,导致聚集状态下的发射增强。这种引人入胜的发光特性使其中一种发光剂能够在纳摩尔浓度的水和有机介质中选择性检测三硝基苯酚(TNP),而不是其他硝基芳族化合物。此外,良好的光稳定性和生物相容性使两种发光剂都能够用作癌细胞成像的荧光生物探针。
更新日期:2020-05-12
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