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Simple Bisthiocarbonohydrazones as Sensitive, Selective, Colorimetric, and Switch‐On Fluorescent Chemosensors for Fluoride Anions
Author(s) -
Han Feng,
Bao Yuhui,
Yang Zhigang,
Fyles Thomas M.,
Zhao Jianzhang,
Peng Xiaojun,
Fan Jiangli,
Wu Yunkou,
Sun Shiguo
Publication year - 2007
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.200600904
Subject(s) - moiety , chemistry , titration , acetonitrile , fluorescence , fluoride , hydrogen bond , absorption (acoustics) , photochemistry , solvent , delocalized electron , molecule , inorganic chemistry , stereochemistry , organic chemistry , materials science , physics , quantum mechanics , composite material
Abstract Bisthiocarbonohydrazones are found to be a class of sensitive, selective, ratiometric, and colorimetric chemosensors for anions such as fluoride (F − ) or acetate (Ac − ). The sensitivities, or the binding constants of the sensors with anions, were found to be strongly dependent on the substituents appended on the π‐conjugation framework, the delocalization bridge CHN, the aromatic moiety, and the hetero atom in the CX group (X=O, S) of the sensors. Single‐crystal structures and 1 H NMR titration analysis shows that the CHN moiety is a hydrogen‐bond donor, and it is proposed that an additional CH⋅⋅⋅F hydrogen bond is formed for the sensors in the presence F − . A sensor bearing anthracenyl groups is demonstrated as a switch‐on fluorescent chemosensor for F − and Ac − . The recognition of F − in acetonitrile (MeCN) by a sensor with nitrophenyl substituents is tolerant to MeOH (MeCN/MeOH=10:1, v/v) and water (MeCN/H 2 O=30:1, v/v); at these solvent ratios the absorption intensity of the sensor–F − complex solution at maximal absorption wavelength was attenuated to half of the original value in pure MeCN.