Core-modified of fluoranthene with "propeller" structure for highly sensitive detection of nitroaromatic compounds.

Abstract

Two fluoranthene derivatives with "propeller" structure, named as 7,8,9,10-tetraphenylfluoranthene (TPFA) and 3-phenoxy-7,8,9,10-tetraphenyl fluoranthene (PO-TPFA), were designed and synthesized by introducing outer phenyl and phenoxy substituents to fluoranthene. Given the steric hindrance of this unique structure, both organic dyes exhibited similar fluorescence spectra and strong fluorescence emission from the solution to the film state. The introduction of a phenoxy group showed obvious influence to the molecular optical properties of fluoranthene. Density functional theory calculations were further conducted to verify this finding. Both dyes were used as fluorescent probes and exhibited and sensitive fluorescence response to nitroaromatic explosives and highly selectivity to picric acid. Furthermore, PO-TPFA exhibited better detection performance to nitroaromatic explosives than TPFA. This work can serve as a guide for molecular fluorescence design because these dyes possess excellent fluorescence in solution and film states and can be used for the sensitive fluorescence detection of nitroaromatic explosives.