A reusable cyanide sensor via activation of C–H group: trifluoromethylcarbinol-directed meta-C–H cyanomethylation of naphthalimide

Abstract

A fluorescent and colorimetric anion sensor based on the activated C–H group has been developed, and its reusability and ability to selectively detect cyanides have been demonstrated. The system utilizes trifluoromethylcarbinol-directed C–H regioselective cyanomethylation for direct C–C bond formation between the fluorophore and acetonitrile. The present paper also describes a novel strategy for the enhancement of carbanion stability by a potential intramolecular CO⋯H–C hydrogen bonding system, thus providing a new way to develop activated CH-based anion receptors.