Blue-Emitting 2-(2'-Hydroxyphenyl)benzazole Fluorophores by Modulation of Excited-State Intramolecular Proton Transfer: Spectroscopic Studies and Theoretical Calculations.

This article describes the synthesis, spectroscopic studies, and theoretical calculations of nine original fluorophores based on the 2-(2'-hydroxyphenyl)benzazole (HBX) scaffold, functionalized at the 4-position of the phenol ring by ethynyl-extended aniline moieties. HBX dyes are well-known to display an excited-state intramolecular proton transfer (ESIPT) process, owing to a strong six-membered hydrogen bond in their structure that allows for an enol/keto tautomerism after photoexcitation. Appropriate electronic substitution can perturb the ESIPT process, leading to dual fluorescence, both excited tautomers emitting at specific wavelengths.