文献类型：期刊文献

英文题名：Comparative study of the dicyanovinyl-functionalized 1,1-dimethyl-2,3,4,5-tetraphenylsilole derivatives on their structures, properties, and applications in thiol detection

作者：Mei, Ju[1,2];Sun, Jing Zhi[4];Qin, Anjun[5];Tang, Ben Zhong[3,5,6]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Hong Kong Univ Sci & Technol, Chinese Natl Engn Res Ctr Tissue Restorat & Recon, Div Biomed Engn,Dept Chem,Hong Kong Branch, Inst Adv Study,Inst Mol Funct Mat,State Key Lab M, Kowloon, Hong Kong, Peoples R China;[4]Zhejiang Univ, Dept Polymer Sci & Engn, MoE Key Lab Macromol Synth & Functionalizat, Hangzhou 310027, Zhejiang, Peoples R China;[5]South China Univ Technol, Guangdong Innovat Res Team, SCUT HKUST Joint Res Lab, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China;[6]HKUST Shenzhen Res Inst, 9 Yuexing 1st RD,Hitech Pk, Shenzhen 518057, Peoples R China

年份：2017

卷号：141

起止页码：366

外文期刊名：DYES AND PIGMENTS

收录：;EI(收录号：20170903404798);WOS:【SCI-EXPANDED(收录号:WOS:000399852700044)】；

基金：This work was financially supported by National Natural Science Foundation of China [grant numbers 21604023, 21490570, 21490574] and sponsored by the Shanghai Sailing Program [grant number 16YF1402200]. The authors thank Prof. Ping Lu from Jilin University for the help in the measurements of solid-state quantum yields.

语种：英文

外文关键词：AIE; ICT; Silole; Structure-property relationship; Ratiometric probes; Thiols

摘要：Integrating electron-accepting dicyanovinyl (DCV) moieties with aggregation-induced emission (AIE)active 1,1-dimethyl-2,3,4,5-tetraphenylsilole (DMTPS) skeleton on the meta-positions of the 2,5-phenyl groups via simple Knoevenagel condensation derived the novel polar silole derivative, i.e. DMTPS-m-DCV. Systematic and comparative studies on the structures, properties and application in the thiol detection of DMTPS-m-DCV and its para-isomer DMTPS-p-DCV shed light on their structure-property relationships. The multiple rotors and non-planar 3D configurations bestow aggregation-enhanced emission (AEE) or AIE feature on them and the A-D-A type electronic structures impart intramolecular charge transfer (ICT) effect to them. The reactive DCV units endow these two isomers with the capability of specifically recognizing thiol species. The subtle variation in the substitution position of DCV units leads to a number of differences in the crystal and electronic structures, thermal stability, fluorescence properties, solvatochromism, ICT effect, thiol-reactivity, and thus detection performances. Benefiting from their AIE/AEE plus ICT attributes, both DMTPS-p-DCV and DMTPS-m-DCV perform well as ratio metric probes for thiols with minimal background noise, remarkable blue shift in fluorescence maxima, large enhancement in fluorescence intensity as well as high contrast in the biocompatible aqueous solutions or on the solid matrices. Intriguingly, DMTPS-p-DCV could differentiate cysteine (Cys) and homocysteine (Hcy) from glutathione (GSH) relying on the distinctive differences in kinetics. The fluorescence turn-on ratiometric probe DMTPS-m-DCV holds a superb sensitivity to Cys with a detection limit lower than 0.5 mu M. Fast and sensitive responses of TLC plates with DMTPS-m-DCV spots to Cys in water demonstrated the practicability of these simple and handy test strips. (C) 2017 Elsevier Ltd. All rights reserved.