Kinetic Co-assembly Pathway Induced Chirality Inversion Along with Morphology Transition

Angew Chem Int Ed Engl. 2022 Nov 14;61(46):e202211812. doi: 10.1002/anie.202211812. Epub 2022 Oct 18.

Abstract

Kinetic co-assembly pathway induced chirality inversion along with morphology transition is of importance to understand biological processes, but still remains a challenge to realize in artificial systems. Herein, helical nanofibers consisting of phenylalanine-based enantiomers (L/DPF) successfully transform into kinetically trapped architectures with opposite helicity through a kinetic co-assembly pathway. By contrast, the co-assemblies obtained by a thermodynamic pathway exhibit non-helical structures. The formation sequence of non-covalent interactions plays a crucial role in structural chirality of co-assemblies. For the kinetic pathway, the hydrogen bonding between D/LPF and naphthylamide derivatives forms before π-π stacking to facilitate the formation of helical structures with inverse handedness. This study may provide an approach to explore chirality inversion accompanied by morphology transition by manipulating the kinetic co-assembly pathway.

Keywords: Chirality Inversion; Co-Assembly; Kinetic Pathway; Morphological Transition; Nanofibers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrogen Bonding
  • Kinetics
  • Phenylalanine*
  • Stereoisomerism
  • Thermodynamics

Substances

  • Phenylalanine