Deracemization of Carbohelicenes by a Chiral Perylene Bisimide Cyclophane Template Catalyst.

ABSTRACT: Deracemization describes the conversion of a racemic mixture of a chiral molecule into an enantioenriched mixture or an enantiopure compound without structural modifications. Herein, we report an inherently chiral perylene bisimide (PBI) cyclophane whose chiral pocket is capable of transforming a racemic mixture of [5]-helicene into an enantioenriched mixture with an enantiomeric excess of 66 %. UV/Vis and fluorescence titration studies reveal this cyclophane host composed of two helically twisted PBI dyes has high binding affinities for the respective homochiral carbohelicene guests, with outstanding binding constants of up to 3.9×10¹⁰  m^-1 for [4]-helicene. 2D NMR studies and single-crystal X-ray analysis demonstrate that the observed strong and enantioselective bin

SUBMITTER: Weh M 

PROVIDER: S-EPMC8362091 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature