Premium
Multiple Hydrogen Bonds Promoted ESIPT and AIE‐active Chiral Salicylaldehyde Hydrazide
Author(s) -
Wang Man,
Cheng Caiqi,
Song Jintong,
Wang Jun,
Zhou Xiangge,
Xiang Haifeng,
Liu Jin
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800115
Subject(s) - chemistry , salicylaldehyde , hydrogen bond , intramolecular force , photochemistry , molecule , fluorescence , intermolecular force , stokes shift , conjugated system , combinatorial chemistry , stereochemistry , organic chemistry , polymer , schiff base , physics , quantum mechanics
The simpler, the better! A series of simple and highly fluorescent salicylaldehyde hydrazide molecules (41 samples) have been designed and prepared. Even though these soft materials contain a very small π‐conjugated system, they can go through multiple intramolecular and intermolecular hydrogen bonds promoted excited‐state intramolecular proton‐transfer (ESIPT) to display strong blue, green, yellow, and orange aggregation‐induced emission (AIE) with large Stokes shifts (up to 184 nm) and high fluorescence quantum yields ( Ф up to 0.20). Unusual mechanochromic fluorescence enhancements are also found in some solid samples. Through coordination, hydrogen and halogen bonds, these flexible molecules can be used as Mg 2+ ( Ф up to 0.46) probes, universal anion ( Ф up to 0.14) and unprotected amino acids ( Ф up to 0.16) probes, and chiral diamine (enantiomeric selectivity and Ф up to 0.36 and 0.062, respectively) receptors. Combining their advantages of AIE and biocompatibility, these low cytotoxic dyes have potential application in living cell imaging. Furthermore, the effects of different functional groups on the molecule arrangement, ESIPT, AIE, probe, and chiral recognition properties are also examined, which provide a simple and bright paradigm for the design of multiple‐stimuli‐responsive smart materials.