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Fluorescent and Colorimetric Probes for Mercury(II): Tunable Structures of Electron Donor and π‐Conjugated Bridge
Author(s) -
Cheng Xiaohong,
Li Shuang,
Jia Huizhen,
Zhong Aoshu,
Zhong Cheng,
Feng Jun,
Qin Jingui,
Li Zhen
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102376
Subject(s) - triphenylamine , fluorescence , conjugated system , chemistry , aldehyde , photochemistry , intramolecular force , acceptor , molecule , electron donor , cyanine , electron acceptor , polymer , organic chemistry , catalysis , physics , quantum mechanics , condensed matter physics
A new series of intramolecular‐charge‐transfer (ICT) molecules (compounds 1 , 2 , and 3 ) were synthesized by attaching various electron‐donating thiophenes groups to a triphenylamine backbone with an aldehyde group as the electron acceptor. Based on the protection reaction between ethanethiol and aldehyde, the corresponding dithioacetals (compounds S1 , S2 , and S3 ) were prepared to serve as novel colorimetric and fluorescent chemosensors for Hg 2+ ions. Also, compound S1 was further utilized to construct the chemical‐reaction‐based conjugated polymer probe ( PS1 ) towards Hg 2+ ions. In the presence of as little as 10 n M Hg 2+ , compound PS1 displayed an apparent change in the fluorescent intensity. The sensing processes were revealed to be mediated by ICT, as confirmed by time‐dependent DFT calculations. Furthermore, compound S1 was successfully applied to microscopic imaging for the detection of Hg 2+ in HeLa cells with ratiometric fluorescent methods.