N‐Heterocyclic Carbene Formation Induced Fluorescent and Colorimetric Sensing of Fluoride Using Perimidinium Derivatives |
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| Authors: | Dawei Zhang Haiqiang Yang Dr. Alexandre Martinez Kelsey Jamieson Dr. Jean‐Pierre Dutasta Prof. Guohua Gao |
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| Affiliation: | 1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062 (China);2. Laboratoire de Chimie, école Normale Supérieure de Lyon, 46, Allée d'Italie, 69364 Lyon (France) |
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| Abstract: | 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. |
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| Keywords: | colorimetric sensors fluorescent sensors fluoride N‐heterocyclic carbine perimidinium |
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