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

作者：Wang, Qin; Xu, Longfei; Niu, Yahui; Wang, Yuxiu; Yuan, Mao-Sen^*; Zhang, Yanrong^*

来源：Dyes and Pigments, 2017, 142: 365-370.

DOI：10.1016/j.dyepig.2016.11.055

• Solid-state fluorescence
• Crystal packing
• Excited state intramolecular proton transfer
• Steric hindrance

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.

• 出版日期2017-7
• 单位西北农林科技大学