A perpendicular phenyl-induced exceedingly efficient solid-state excited state intramolecular proton transfer fluorophore based on 2-(2-hydroxyphenyl)benzothiazole

Fluorescent solid-state organic materials have been intensively researched in recent years. In this study, two 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives: phenylethylene-modified HBT (HBT-s-Ph) and diphenylethylene-modified HBT (HBT-d-Ph), were synthesized by facile Suzuki cross-coupling reactions. In toluene solutions, the fluorescence quantum yield (Phi(f)) of HBT-s-Ph is slightly larger than that of HBT-d-Ph, because of the presence of a stronger intramolecular H-bond in HBT-s-Ph than in HBT-d-Ph. In crystalline forms, both of their Phi(f) has substantial improvement, and the Phi(f) of HBT-d-Ph reaches 78%, which is twice that of HBT-s-Ph. The crystal structure revealed that the striking emission enhancement of HBT-d-Ph was attributable to its distinct molecular packing model and the resultant relatively weak intermolecular interactions induced by the single phenyl group cis to the HBT moiety. (C) 2016 Elsevier Ltd. All rights reserved.