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

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. A triphenylamine “core” decorated by methyl acrylate groups is identified as a functional candidate for gel formation. The gel–sol transformation can be achieved upon heating or cooling. π–π stacking and the interaction between the superimposed phenyl and carbonyl groups are the interaction forces. What is more, this interaction model can be regarded as a powerful tool in the construction of supramolecules.