title: N-heterocyclic carbene formation induced fluorescent and colorimetric sensing of fluoride using perimidinium derivatives.
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.
authors.affiliation: Shanghai 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).
authors.forename: Dawei
authors.initials: D
authors.lastname: Zhang
authors.forename: Haiqiang
authors.initials: H
authors.lastname: Yang
authors.forename: Alexandre
authors.initials: A
authors.lastname: Martinez
authors.forename: Kelsey
authors.initials: K
authors.lastname: Jamieson
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Dutasta
authors.forename: Guohua
authors.initials: G
authors.lastname: Gao
keywords: N-heterocyclic carbine; colorimetric sensors; fluorescent sensors; fluoride; perimidinium