Self-Assembly of Tetraphenylethylene-Based Amphiphiles in Aqueous Methanol Solution into Two-Dimensional Chiral...

Most synthetic building blocks self-assemble into one- or three-dimensional architectures. However, fewer examples have been reported on the aggregation of amphiphiles to form optically-active two-dimensional (2D) structures. Herein, we report the self-assembly of tetraphenylethylene (TPE)-containing hydrophilic dendrons into 2D sheet structures in aqueous methanol solution. TEM and AFM investigations showed that the self-assembly of disubstituted TPE generates helical nanofibers as an intermediate structure which, in turn, laterally associate into a chiral sheet structure with a thickness of 4.6 nm, whereas tetrasubstituted TPE self-assembles into a nonchiral sheet structure with a thickness of 3.8 nm. In great contrast to the nonchiral sheets, the chiral sheets are able to preferentially absorb the d-enantiomer in a racemic phenylalanine derivative solution accompanied by fluorescence enhancement, thus indicating that the single-layered chiral sheets act as an enantioselective membrane that can be used for fluorescence sensing.