Triphenylamine‐Based Fluorescent Soft Matter: Interlaced Methyl Cinnamate Groups as the Dominant Interaction Tools for Gel Formation

Triphenylamine‐Based Fluorescent Soft Matter: Interlaced Methyl Cinnamate Groups as the... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Macromolecular Chemistry and Physics Wiley

Triphenylamine‐Based Fluorescent Soft Matter: Interlaced Methyl Cinnamate Groups as the Dominant Interaction Tools for Gel Formation

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Publisher
Wiley
Copyright
© Copyright 2014 by WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
1022-1352
eISSN
1521-3935
D.O.I.
10.1002/macp.201400357
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Macromolecular Chemistry and PhysicsWiley

Published: Jan 1, 2014

Keywords: ; ; ; ;

References

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