Resorcinarenes represent a versatile framework for enforced cavity molecules, or cavitands, for applications such as sensors, immiscible polymer binding, photosensitive switches, and polydentate ligand frameworks. Resorcin[4]arene is a stable and readily prepared structure for cavitand foundations. With eight hydroxyl groups spanning the molecular crown and four trailing R groups extending out the cavity base, resorcin[4]arenes have many possibilities for synthetic manipulation. Dichloroquinoxaline has been regularly used reported to bridge adjacent hydroxyl groups to various degrees at different positions, allowing for controlled structural substitution about the rim of the cavitand. Resorcin[4]arene R groups can be selected to provide appropriate solubility for subsequent reactions and applications. Studies have reported good yields of resorcin[4]arene synthesis under large-scale conditions with C5 hydrocarbon tails versus poor yields with C11 hydrocarbon tails. A current issue in our lab is the purification of resorcin[4]arene by recrystallization. This poster aims to compare the purification of the two resorcin[4]arene analogs along with a comparison of the purification methods for quinoxaline and methylene-bridged derivatives. The variables tested were a partial purification, solvent system, and scale. The results of the purifications will be reported in this work.

Diquinoxaline, dimethylene-bridged resorcin[4]arene cavitand synthesis and purification

2019 Spring National Meeting

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