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Triphenylamine‐Based Fluorescent Soft Matter: Interlaced Methyl Cinnamate Groups as the Dominant Interaction Tools for Gel Formation
Author(s) -
Ma Hengchang,
Ma Yuan,
Li Wenfeng,
Wang Feng,
Zhu Fuping,
Qi Chunxuan,
Zhang Zhongwei,
Yao Xiaoqiang,
Lei Ziqiang
Publication year - 2014
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201400357
Subject(s) - triphenylamine , stacking , supramolecular chemistry , chemistry , fluorescence , methyl acrylate , soft matter , polymer chemistry , materials science , copolymer , crystallography , polymer , organic chemistry , crystal structure , physics , colloid , quantum mechanics
Novel low‐molecular‐weight organic gelators (LMOGs) with propeller‐shaped triphenylamine as a “core” and tiny methyl acrylate groups as “tails,” are developed, which would not be thought to be a candidate for gel formation due to the absence of planar rigid aromatic building blocks and long‐chain alkyls. The sensitive gel–sol transformation can be easily achieved upon heating or cooling accompanied by molecular aggregation or disaggregation. H–H 2D NOESY is employed to prove that the π–π stacking between the interlaced tiny “tails” and the interaction between the superimposed phenyl and carbonyl groups of adjacent molecules are the dominant interaction forces. What is more, this soft interaction model can be regarded as a powerful tool in the design and construction of supramolecular structures in the future. At present, tris(4‐methyl cinnamate)amine synthesized by a single step, but with a gel‐formation ability and an aggregation‐induced fluorescence emission property, has great potential application as functional soft matter in amorphous materials, photoelectric materials, and so on.