Angewandte Chemie | 2019
Chiral Supramolecular Nano-Architectures from Macroscopic Mechanical Rotations: Effects on Chiral Aggregation Behavior of Phthalocyanines.
Abstract
Fluid dynamics, resulting from the macroscopic mechanical rotation of a rotary evaporator or a magnetic stirrer, has been shown to selectively induce one of two enantiomers (mirror-image structures) in certain nanoscale supramolecules. This has attracted considerable attention from the viewpoint of novel synthetic methods for chiral molecules and provides a clue to explain the biased distribution of L-amino acids and D-sugars in biological systems (the homochirality of life). As an alternative to giving a chiral twist to synthesized supramolecules or polymers, it is a challenge to reproducibly prepare chiral species only by macroscopic mechanical rotations. We demonstrate a highly reproducible method for rotary evaporation-induced chiral H-aggregation of achiral phthalocyanines, and propose chiral induction mechanisms by using the chiroptical sign-based absolute structures. We propose that these results will provide insight to the origin of the homochirality of life, and this will be a pioneering study in a novel scientific field in terms of admixing nanoscale molecular chemistry and macroscopic fluid dynamics.