Singlet oxygen stimulus for switchable functional organic cages.

ABSTRACT: Molecular cages 1a and 2a incorporating a 9,10-diphenylanthracene (DPA) chromophore were synthesized through a templated ring-closure metathesis approach that allows variation in cavity size through the introduction of up to three different pillars. Reversible Diels-Alder reaction between the DPA moiety and photogenerated singlet oxygen smoothly converted 1a and 2a to the corresponding endoperoxide cages 1b and 2b, which are converted back to 1a and 2a upon heating. Endoperoxide formation constitutes a reversible covalent signal that combines structural changes in the interior of the cage with introduction of two additional coordination sites. This results in a large modulation of the binding ability of the receptors attributed to a c

SUBMITTER: Mongin C 

PROVIDER: S-EPMC8150101 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature