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Dicyanomethylene‐benzopyran‐based alkynyl conjugatable near–infrared fluorescent probe for detection of fluoride anion
Author(s) -
Xu Longfei,
Wang Qin,
Yuan MaoSen,
Zhang Yanrong
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201500049
Subject(s) - fluorescence , fluorophore , conjugate , conjugated system , chemistry , molecule , moiety , photochemistry , combinatorial chemistry , lipophilicity , biocompatibility , click chemistry , organic chemistry , polymer , mathematical analysis , physics , mathematics , quantum mechanics
Near‐infrared (NIR) fluorophore with one functional group, which can be utilized to conjugate other molecules, could meet various requirements just through structural modification, such as for regulating their subtle equilibrium between hydrophilicity and lipophilicity. Herein, considering the favorable photophysical properties of dicyanomethylene‐benzopyran (DCMB) derivatives and the orthogonality of functional groups and the excellent biocompatibility of Cu I ‐catalyzed click chemistry, the synthesis of azido and phenolic hydroxyl‐bifunctionalized DCMB‐based compound N 3 ‐DCMBOH is described, which can conjugate with other molecules by click chemistry. As a preliminary exploration, tert ‐butyldiphenylsilyl group and alkynyl‐contained quaternary ammonium were successively conjugated onto N 3 ‐DCMBOH to construct NIR fluorescent sensor QA‐DCMBSi for detection of F − . The dramatic absorption band change with 196 nm red shift and distinct NIR fluorescence enhancement at 718 nm, can be attributed to F − mediated cleavage of silicon‐oxygen bond to release QA‐DCMBOH, which was verified by MS spectrum.