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Pyridinium‐Fused Pyridinone: A Novel “Turn‐on” Fluorescent Chemodosimeter for Cyanide
Author(s) -
Li Junbo,
Gao Junkuo,
Xiong WeiWei,
Li PeiZhou,
Zhang Huacheng,
Zhao Yanli,
Zhang Qichun
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201301144
Subject(s) - pyridinium , fluorescence , cyanide , turn (biochemistry) , chemistry , photochemistry , combinatorial chemistry , organic chemistry , biochemistry , optics , physics
Abstract A new chemodosimeter based on pyridinium‐fused pyridinone iodide ( PI ) has been obtained through a “clean reaction” method. This compound can detect CN − in aqueous solution with a high selectivity and rapid response. The detection of CN − occurs through the nucleophilic attack of CN − on the CN bond, which induces the destruction of the π‐conjugation on the pyridinium ring. Support of this detection mechanism was obtained by 1 H NMR titration, HR‐MS, and DFT calculations. Upon the addition of 10 equivalents CN − to a solution of PI in THF/H 2 O (1:1, v/v), a 57‐fold enhancement in fluorescence intensity was observed at the maximum emission wavelength of 457 nm. Meanwhile, the maximum absorption wavelength was also blue‐shifted from 447 nm to 355 nm. Other common anions such as BF 4 − , PF 6 − , F − , Cl − , Br − , I − , H 2 PO 4 − , ClO 4 − , CH 3 COO − , NO 2 − , N 3 − , and SCN − had little effect on the detection of CN − . The response time of PI for CN − was less than 5 seconds. The detection limit was calculated to be 5.4×10 −8 M , which is lower than the maximum permission concentration in drinking water (1.9 μ M ) set by the World Health Organization (WHO).