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一种具有 ESIPT 和 AIE 性质的红色发光苯并噻唑基荧光团及其用于检测和成像次氯酸的应用。

A red-emissive benzothiazole-based luminophore with ESIPT and AIE natures and its application for detecting and imaging hypochlorous acid.

机构信息

Key Laboratory of Chemical Sensing and Catalysis, Hengyang Key Laboratory of New Detection Technology and Biological Agents of Animal Microorganism, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang 421008, PR China.

Key Laboratory of Chemical Sensing and Catalysis, Hengyang Key Laboratory of New Detection Technology and Biological Agents of Animal Microorganism, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang 421008, PR China.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2022 Nov 15;281:121601. doi: 10.1016/j.saa.2022.121601. Epub 2022 Jul 6.

DOI:10.1016/j.saa.2022.121601
PMID:35816864
Abstract

A new "ESIPT + AIE" based dye of benzothiazole with red emission and a large Stokes shift was constructed by combining 2-(2'-hydroxyphenyl)benzothiazole as the ESIPT unit and α-cyanostilbene as the AIE unit. The compound BACN was found to be a ideal HClO chemosensor, and presented palpable fluorescence and colorimetric responses toward HClO via the HClO-trigged oxidation cleavage of the ethylene bridge activated by the electron withdrawing cyano group. BACN was capable of recognizing HClO rapidly (12 s) and sensitively under physiological conditions, with good selectivity over other biologically pertinent substances. Thanks to strong red emission (λ = 606 nm) and large Stokes shift (213 nm) resulted from the combination of ESIPT and AIE effects, it was successfully utilized for the recognition of exogenous and endogenous HClO in living HeLa cells.

摘要

一种新型的基于苯并噻唑的“ESIPT+AIE”染料,具有红色发射和大斯托克斯位移,是通过将 2-(2'-羟基苯基)苯并噻唑作为 ESIPT 单元和α-氰基二苯乙烯作为 AIE 单元组合而成的。研究发现化合物 BACN 是一种理想的 HClO 化学传感器,通过电子受主氰基基团激活的乙烯桥的 HClO 触发氧化裂解,对 HClO 表现出明显的荧光和比色响应。在生理条件下,BACN 能够快速(12 s)和灵敏地识别 HClO,对其他生物相关物质具有良好的选择性。由于 ESIPT 和 AIE 效应的结合产生了强的红色发射(λ=606 nm)和大的斯托克斯位移(213 nm),它成功地用于活 HeLa 细胞中外源和内源性 HClO 的识别。

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引用本文的文献

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Review on Synthesis of 2-(2-Hydroxyaryl) Benzothiazoles (HBT) for Excited-State Intra-molecular Proton Transfer (ESIPT)-Based Detection of Ions and Biomolecules.基于激发态分子内质子转移(ESIPT)的离子和生物分子检测的2-(2-羟基芳基)苯并噻唑(HBT)合成综述
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The Synergistic Mechanisms of AIE, ESIPT and ICT in the α-cyanostilbene-based Derivative: A Red-fluorescence Probe With a Large Stokes' Shift for Copper (II) Ion Determination and Reversible Response to Amine/acid Vapor.
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