Kinetic Trapping of Rylene Diimide Covalent Organic Cages

22 August 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Formation of imine organic cages relies on error-correction of dynamic covalent chemistry. Here, we demonstrate kinetically-trapped rylene diimide cages formed in high yields and we investigate the effect of substituents on their formation kinetics and stability. Thereby, we identified that alkoxy groups in triformylbenzene, used to stabilize covalent organic cages or COFs, act as stereoelectronic chameleons. We underscore critical factors governing the chemistry of kinetically-trapped imine assemblies like sterics, electronics, catalysis, and water concentration.

Keywords

Covalent organic cages
Porous organic cages
Dynamic covalent chemistry
Imine chemistry
Kinetic control
Stereoelectronic effect

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