N-heterocyclic carbene formation induced fluorescent and colorimetric sensing of fluoride using perimidinium derivatives

Dawei Zhang; Haiqiang Yang; Alexandre Martinez; Kelsey Jamieson; Jean-Pierre Dutasta; Guohua Gao

doi:10.1002/chem.201404806

N-heterocyclic carbene formation induced fluorescent and colorimetric sensing of fluoride using perimidinium derivatives

Chemistry. 2014 Dec 15;20(51):17161-7. doi: 10.1002/chem.201404806. Epub 2014 Oct 24.

Authors

Dawei Zhang¹, Haiqiang Yang, Alexandre Martinez, Kelsey Jamieson, Jean-Pierre Dutasta, Guohua Gao

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); Laboratoire de Chimie, École Normale Supérieure de Lyon, 46, Allée d'Italie, 69364 Lyon (France).

PMID: 25346203
DOI: 10.1002/chem.201404806

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.

Keywords: N-heterocyclic carbine; colorimetric sensors; fluorescent sensors; fluoride; perimidinium.