This project explores the effect of replacing one or two quinoxaline moieties with benzal groups in a molecular capsule composed of two resorcin[4]arene based cavitands linked by a rigid tetraazaanthracene bridge. Guest binding was not observed in a previously published molecular capsule which included only quinoxaline groups as it was too flexible. Upon the addition of benzal moieties a more rigid structure is expected which can improve the ability of the capsule to bind to a guest. Keeping at least one quinoxaline moiety will allow the capsule to change conformations from kite(open) to vase(closed) conversely. These conformational changes can be achieved by altering the temperature, pH or solvent polarity. Such ability can be exploited in molecular recognition, catalysis and toxin remediation. In addition, the free rotation along the single bond in the benzal moiety can serve as gateway for small compounds. Capsules have been partially synthesized, and intermediates have been characterized by <sup>1</sup>H NMR. Further <sup>1</sup>H NMR studies will determine the degree to which the capsules can change conformation under different conditions.

Synthesis of a resorcin[4]arene based benzal-quinoxaline heterocapsule

2019 Spring National Meeting

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