β-Cyclodextrin-Promoted Colorimetric and Fluorescence Turn-on Probe for Discriminating Highly Toxic Thiophenol from Biothiols,ACS Sustainable Chemistry & Engineering

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β-Cyclodextrin-Promoted Colorimetric and Fluorescence Turn-on Probe for Discriminating Highly Toxic Thiophenol from Biothiols
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-04-13 , DOI: 10.1021/acssuschemeng.0c00766
Ting Xu ₁ , Shaojing Zhao ₁ , Xiaoli Wu ₂ , Lintao Zeng ₂ , Minhuan Lan _{1,

3}

Affiliation

A complex that was composed of β-cyclodextrin (β-CD) and a flavone derivative (compound 5) was designed as a colorimetric and fluorescence turn-on probe to discriminate thiophenol (PhSH) from biothiols in environmental water samples. The probe worked via a combination of photoinduced electron transfer (PET) and excited-state intramolecular proton transfer (ESIPT) mechanisms. In this complex (β-CD-5), the 2,4-dinitrobenzenesulfonyl group efficiently quenched the fluorescence of compound 5 through a PET mechanism, and sulfonate was cleaved by PhSH to produce a compound that has strong fluorescence. Meanwhile, ESIPT fluorescence that originated from the flavone was observed. Significantly, β-CD improved the response time and sensitivity of compound 5 with respect to PhSH. Under optimized conditions, the response time was 5 min, and the limit of detection of β-CD-5 for PhSH was ∼2.8 nM. The outstanding sensing performance of β-CD-5 was demonstrated to be originated from the geometric match between compound 5 and β-CD and enrichment of PhSH in the β-CD cavity.

中文翻译：

β-环糊精促进的比色和荧光开启探针用于区分生物硫醇中的高毒性硫酚

设计一种由β-环糊精（β-CD）和黄酮衍生物（化合物5）组成的复合物作为比色和荧光开启探针，以区分环境水样品中的生物酚中的硫酚（PhSH）。该探针通过光致电子转移（PET）和激发态分子内质子转移（ESIPT）机制的结合来工作。在该络合物（β-CD- 5）中，2，4-二硝基苯磺酰基通过PET机理有效地淬灭了化合物5的荧光，并且磺酸盐被PhSH裂解以产生具有强荧光的化合物。同时，观察到源自黄酮的ESIPT荧光。值得注意的是，β-CD改善了化合物的响应时间和灵敏度5相对于加入PhSH。在最佳条件下，反应时间为5分钟，β-CD- 5对PhSH的检出限为〜2.8 nM。已证明β-CD- 5的出色传感性能源自化合物5和β-CD之间的几何匹配以及β-CD腔中PhSH的富集。

更新日期：2020-04-23

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