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N-heterocyclic carbene formation induced fluorescent and colorimetric sensing of fluoride using perimidinium
Dawei Zhang1, Haiqiang Yang, Alexandre Martinez
1Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062 (China); Laboratoire de Chimie, École Normale Supérieure de Lyon, 46, Allée d'Italie, 69364 Lyon (France).
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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