Mutual induced fit transition structure stabilization of corannulene's bowl-to-bowl inversion in a perylene bisimide cyclophane.

ABSTRACT: Corannulene is known to undergo a fast bowl-to-bowl inversion at r.t. via a planar transition structure (TS). Herein we present the catalysis of this process within a perylene bisimide (PBI) cyclophane composed of chirally twisted, non-planar chromophores, linked by para-xylylene spacers. Variable temperature NMR studies reveal that the bowl-to-bowl inversion is significantly accelerated within the cyclophane template despite the structural non-complementarity between the binding site of the host and the TS of the guest. The observed acceleration corresponds to a decrease in the bowl-to-bowl inversion barrier of 11.6 kJ mol^-1 compared to the uncatalyzed process. Comparative binding studies for corannulene (20 π-electrons) and other planar polycyclic aromatic hydroc

SUBMITTER: Weh M 

PROVIDER: S-EPMC10762775 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature