Enantioselective synthesis of chiral porphyrin macrocyclic hosts and kinetic enantiorecognition of viologen guests.

ABSTRACT: The construction of macromolecular hosts that are able to thread chiral guests in a stereoselective fashion is a big challenge. We herein describe the asymmetric synthesis of two enantiomeric C ₂-symmetric porphyrin macrocyclic hosts that thread and bind different viologen guests. Time-resolved fluorescence studies show that these hosts display a factor 3 kinetic preference (ΔΔG ^‡ _on = 3 kJ mol^-1) for threading onto the different enantiomers of a viologen guest appended with bulky chiral 1-phenylethoxy termini. A smaller kinetic selectivity (ΔΔG ^‡ _on = 1 kJ mol^-1) is observed for viologens equipped with small chiral sec-butoxy termini. Kinetic selectivity is absent when the C

SUBMITTER: Gilissen PJ 

PROVIDER: S-EPMC8179042 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature