Hydrogen bond and nucleophilicity motifs in the design of molecular probes for CN− and F− ions

In this study, we have designed and synthesized two excited-state proton transfer (ESIPT)-active fluorescent probes (1, 2) that can form nanoscopic self-assembly in pure aqueous medium. The extent of self-assembly was found to be prominent for compound 2 having the hydroxyl unit compared to that witnessed for 1 possessing the amino functional group at the same position. In both cases, the color of the solution changed upon the addition of the CN − ion. Compound 1 exhibited a superior response toward the CN − ion with a red-shifted fluorescence maximum, while the addition of CN − resulted in a blue-shifted λmax for 2 with a relatively poor response. The mechanistic investigations indicated that both the salicylaldimine and hydrazone units participated in the hydrogen bonding interactions with the cyanide ions. Thus, we believe that the differences in response toward the CN − ion were attributed to both changes in the protonation equilibrium of the compounds along with the extent of aggregation. Given this high sensitivity, we employed this system to analyze cyanide in different natural water samples. The obtained high percentage recovery values (∼100%) and significantly low relative standard deviations (<5%) indicate that semiquantitative analysis of cyanide is achievable using this method. Also, chemically modified paper strips have been designed for rapid, on-location detection as well as quantification of CN − ions via naked-eye color-changing response.

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Hydrogen bond and nucleophilicity motifs in the design of molecular probes for CN− and F− ions

Cited by 2 publications

References 118 publications

Photo responsive dyads for fast recognition of cyanide and fluoride in aqueous media

Photo responsive dyads for fast recognition of cyanide and fluoride in aqueous media

Design of ESIPT-Based Fluorescent Probes for Dual-Mode Sensing of Cyanide: Application to Rapid On-Location Detection and Screening of Natural Water Samples

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