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N‐Heterocyclic Carbene Formation Induced Fluorescent and Colorimetric Sensing of Fluoride Using Perimidinium Derivatives
Author(s) -
Zhang Dawei,
Yang Haiqiang,
Martinez Alexandre,
Jamieson Kelsey,
Dutasta JeanPierre,
Gao Guohua
Publication year - 2014
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.201404806
Subject(s) - fluorescence , carbene , deprotonation , disproportionation , chemistry , fluoride , photochemistry , redox , organic chemistry , inorganic chemistry , catalysis , ion , physics , quantum mechanics
In this study, two perimidinium derivatives ( 1 and 2 ) were designed, synthesized, and developed as efficient fluorescent and colorimetric chemodosisensors for F − in DMSO or more competitive media (DMSO containing 10 % water). In the presence of F − , the yellow and non‐fluorescent solution of 1/2 became colourless and exhibited strong blue fluorescence. This unique spectroscopic behaviour of 1/2 towards F − was attributed to the formation of N‐heterocyclic carbene deprotonated by F − , which immediately reacted with water to give a colourless and fluorescent carbinol. Interestingly, it was found that this carbinol intermediate was unstable and further underwent a redox disproportionation to generate two other optically changed compounds. All the proposed mechanisms for the sensing process have been carefully confirmed by experiments.