The key role of chirality and peripheral substitution in the columnar organization of bowl-shaped subphthalocyanines.

ABSTRACT: The columnar arrangement of bowl-shaped aromatics is a promising strategy for producing high-performing semiconductors. However, the structural factors that dictate the self-assembly of these molecules remain poorly understood. Herein, we show how chirality and peripheral substitution affect the columnar assembly of subphthalocyanines (SubPcs) in solution. Both aspects are found to influence the structure, stability, and formation mechanism of the supramolecular polymer obtained. Whereas enantiopure tri-substituted SubPcs cooperatively polymerize into homochiral head-to-tail arrays, racemic mixtures socially self-sort, leading to heterochiral columnar polymers. In sharp contrast, hexa-substituted SubPcs polymerize following an isodesmic mechanism, producing highly robust columnar systems.

SUBMITTER: Labella J 

PROVIDER: S-EPMC11352688 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature