Off–on fluorometric detection of cyanide anions in an aqueous mixture by an indane-based receptor†
Masaya Nakamura,Tetsuri Kogure,Takayuki Hirai
New Journal of Chemistry Pub Date : 11/25/2015 00:00:00 , DOI:10.1039/C5NJ02873F
Abstract

We synthesized an indanedione–coumarin dyad (1) and used it as an off–on type fluorescent receptor for rapid, selective, and sensitive detection of CN in an aqueous mixture. The receptor itself shows very weak fluorescence from the coumarin moiety due to the photoinduced electron transfer (PET) from the photoexcited coumarin to the indanedione moiety. Selective nucleophilic addition of CN to the β-carbon of the receptor suppresses the PET and results in strong fluorescence enhancement. The reaction mechanism was fully confirmed by 1H, 13C NMR, Job's plot, and FAB-MS analysis. The receptor successfully detects CN as low as 25 μM within 20 min.

Graphical abstract: Off–on fluorometric detection of cyanide anions in an aqueous mixture by an indane-based receptor