CLAS: Colby Liberal Arts Symposium

Synthesis and Properties of Oxacalix[2]naphthalimide[2]naphthyridines

Diamond 141

Synthetic organic chemistry is a field where chemists use either established reactions or new methods to form molecules which have not been made before. The Katz Group has focused on a class of molecules called oxacalix[4]arenes. Oxacalix[4]arenes are easily synthesized in high yield, but they have not been extensively studied in the organic chemistry community. This talk focuses on the synthesis and applications of an oxacalix[4]arene with two benzene rings on each side, which is called an oxacalix[2]naphthalimide[2]naphthyridine. The two benzene rings expand the cavity size to ~7 Angstroms (~0.7 nanometers) from ~4.5 Angstroms with one benzene ring on each side, and the 1,3-alternate conformation of the 3-D structure of the oxacalix[4]arenes allows for binding of small aromatic molecules in the cavity. This makes the compound into a molecular tweezer which can pick up the small aromatic molecule and hold it in the cavity. These compounds also have interesting fluorescence properties due to the amount of conjugation, and the fluorescence changes when different groups are added. Present work is focusing on synthesizing variations of the oxacalix[2]naphthalimide[2]naphthyridine and then studying the new molecule for different fluorescence and guest-host properties.

https://digitalcommons.colby.edu/clas/2015/program/234