Microwave-assisted synthesis of a new series of resorcin[4]arene cavitand-capped porphyrin capsules

Abstract

Capsule-shaped molecular receptors are fundamental to the modeling of biological host-guest interactions such as those characteristic of enzymatic processes. Among the more versatile and effective synthetic receptors are the hemicarcerand-type hosts. Herein we report the synthesis of six novel resorcin[4]arene cavitand-capped porphyrin capsules, in a new series of molecular capsules modeled on the classical hemicarcerands initially reported by Cram and co-workers. In the first reported instance of its utilisation in the preparation of supramolecularly-capped porphyrin host molecules, microwave (MW) irradiation was used (in conjunction with Adler conditions) in order to form the porphyrin cap in situ. Additionally, the yields obtained via these conditions exhibited a significant improvement, relative to the traditional refluxing protocol hitherto reported. Capsules 20-25 are indefinitely stable, and we observed that 22 and 25 possess the smallest rigidified cavities yet reported for resorcin[4]arene cavitand-capped porphyrin host molecules.