Hydrogen bond

Non-covalent interactions

Photocatalysis

Acceptor

Electron acceptor

Molecule

Ground state

Electron transfer

Catalysis

Fullerene

Diimide

Quantum mechanics

Condensed matter physics

Artificial photosynthesis

Electron donor

Organic chemistry

BODIPY

Chemical physics

Intermolecular force

Perylene

Chemistry

Photoinduced electron transfer

Photochemistry

Fluorescence

Physics

Journal of the American Chemical Society

The powerful electron accepting ability of fullerenes makes them ubiquitous components in biomimetic donor–acceptor systems that model the intermolecular electron transfer processes of Nature's photosynthetic center. Exploiting perylene diimides (PDIs) as components in cyclic host systems for the noncovalent recognition of fullerenes is unprecedented, in part because archetypal PDIs are also electron deficient, making dyad assembly formation electronically unfavorable. To address this, we report the strategic design and synthesis of a novel large, macrocyclic receptor composed of two covalently strapped electron-rich bis-pyrrolidine PDI panels, nicknamed the "Green Box" due to its color. Through the principle of electronic complementarity, the Green Box exhibits strong recognition of pristine fullerenes (C60/70), with the noncovalent ground and excited state interactions that occur upon fullerene guest encapsulation characterized by a range of techniques including electronic absorption, fluorescence emission,...

The Green Box: An Electronically Versatile Perylene Diimide Macrocyclic Host for Fullerenes