Azobenzene is a light sensitive material that undergoes cis-trans isomerization under specific photochemical conditions. This project consists of the synthesis of a series of these molecular containers that have applications in drug delivery, fuel storage, and environmental remediation. In this project, an azobenzene core capped by two calix[4]arene groups was synthesized. The container is a calix[4]arene-capped azobenzene host consisting of two hemispheric hosts tethered by an azobenzene linker. In previous research, CCA-1, calix[4]arene-capped azobenzene (R group= CH2CH2CH3) was synthesized. To improve the solubility of the molecule in organic solvents, this project was focused on synthesizing CCA-2, calix[4]arene-capped azobenzene with R group= CH2CH2OCH3. It is predicted that the solubility is greater in CCA-2 compared to CCA-1 due to the added methoxy groups. The three main goals of the synthesis were (1) optimizing the synthetic pathway towards the target compound, (2) characterizing each compound in the multi-step process and (3) obtaining solubility data for each compound. Current efforts are focused on analyzing the solubility of both CCA-1 and CCA-2 and their photochemical behavior.

Improved synthesis of a highly soluble calix[4]arene- capped azobenzene

255th National Meeting (2018)

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