Structurally regular arrangement induced fluorescence enhancement and specific recognition for glutathione of a pyrene chalcone derivative

Highlights: • A pyrene chalcone compound as specific probe for GSH was developed. • The probe has high sensitivity, fast response rate and high specificity for GSH. • Structurally regular rodlike crystal was formed in isometric methanol-water solution. • The probe exhibits strong blue fluorescence in isometric methanol-water solution. • The probe can be successfully applied for bioimaging in living cell. -- Abstract: Glutathione (GSH) is an important antioxygen and free radical scavenger in the organism. Level of GSH in vivo is associated with many diseases and specific recognition for GSH is very important. Here, a pyrene chalcone derivative 1 1-(2-hydroxyphenyl)-3-(1-pyrenyl)-2-propen-1-one as specific probe for GSH was developed. The probe can give rise to rapid blue fluorescence enhancement for GSH based on Michael addition reaction in pure PBS solution with high sensitivity, fast response rate and high specificity. The compound also can be applied for GSH detection in HeLa cell. Simultaneously, the compound exhibits blue fluorescence emission enhancement in methanol-water (1:1, v/v) solution with fluorescence quantum yield being 0.45 due to the competition of water molecules for hydrogen bonds between hydroxyl and carbonyl and the formation of structurally regular rodlike crystals, which allows regulating fluorescence emission by different solvent condition.