Selective fluorescent and colorimetric recognition of cyanide via altering hydrogen bonding interaction in aqueous solution and its application in bioimaging

• A new pyrene imine derivative 1 is synthesized for fluorescent and colorimetric sensing of cyanide.
• In an aqueous CH3CN–H2O medium, a selective fluorescence enhancement with cyanide was observed.
• The fluorescent change of 1 with cyanide is attributed to alteration of intramolecular hydrogen bonding.
• Fluorescent probe 1 demonstrated its ability in fluorescent imaging cellular cyanide in living HeLa cells.

In this paper, we report a new pyrene imine derivative which bears a relatively rigid intramolecular hydrogen bonding pocket, for fluorescent and colorimetric sensing of cyanide. In CH3CN solution, the chemosensor displayed distinct fluorescent and UV absorption changes towards CN−, CH3CO2−, F−, and H2PO4−. Notably, in an aqueous CH3CN medium (10%, v/v), the selectivity towards cyanide over other various anions were observed with an obvious fluorescence enhancement and colorimetric change. Thus, we demonstrated that the selectivity of the pyrene based chemosensor towards anions can be optimized via controlling hydrogen bonding interactions in different solvent systems. Finally the application of the chemosensor in fluorescent imaging cellular cyanide variation was demonstrated with living HeLa cells.

Figure optionsDownload as PowerPoint slide