Calixarene-capped azobenzene (CCA) is a light-activated molecular container that contains two calix[4]arene units connected by an azo linker. The linker enables cis-trans photoisomerization, which potentially allows CCA to catch and release cationic guest species as it switches between closed and open forms. Previous shows that CCA with a phenylene spacer between the calix[4]arene and azo moieties binds guest species loosely, presumably because the distance between the convergent calixarene units is too great. This project focuses on the multi-step synthesis of a next-generation CCA that lacks those phenylene spacers. The shorter space between calix[4]arene hemispheres potentially enhances the binding strength of the CCA with pyridinium derivatives due to the decreased distance between host and guest. In the synthesis of this compound, several steps have been optimized from the literature. Future work will focus on the photochemical properties and supramolecular chemistry of this new CCA.

Synthesis of a short-tethered calixarene-capped azobenzene

255th National Meeting (2018)

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