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Tetrathienylethene‐based Positional Isomers with Aggregation‐induced Emission Enabling Super Red‐shifted Reversible Mechanochromism and Naked‐eye Sensing of Hydrazine Vapor
Author(s) -
Song Wenting,
Zhi Junge,
Wang Tianyang,
Li Bo,
Ni Shanshan,
Ye Yanchun,
Wang JinLiang
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901097
Subject(s) - photochemistry , naked eye , chemistry , fluorescence , physics , optics
AIE‐active positional isomers, TTE‐ o ‐PhCHO , TTE‐ m ‐PhCHO and TTE‐ p ‐PhCHO , tetrathienylethene ( TTE) derivates with peripherally attached ortho‐/meta‐/para ‐formyl phenyl groups, were designed and synthesized. The formyl substitution position can effectively modulate their photophysical properties, mechanochromism and fluorescent response to hydrazine. TTE‐ o ‐PhCHO and TTE‐ m ‐PhCHO exhibit remarkable AIE characteristics, and TTE‐ p ‐PhCHO possesses aggregation‐induced emission enhancement performance. They all exhibit high contrast mechanochromism, and TTE‐ m ‐PhCHO shows larger red‐shift (164 nm) than TTE‐ o ‐PhCHO (104 nm) and TTE‐ p ‐PhCHO (125 nm) due to the more twisted molecular conformation and much looser molecular packing. Moreover, TTE‐ o ‐PhCHO with a higher contrast color change can be used as ink‐free rewritable paper. In addition, TTE‐ p ‐PhCHO , as a turn‐on fluorescent probe, can selectively detect hydrazine with significant color changes that are visible by the naked eye . Therefore, the position dependence of groups would be an effective method to modulate the molecular arrangement, as well as develop AIE compounds for mechano‐stimuli responsive materials, ink‐free rewritable papers and chemosensors.