DESIGNING BISCAVITAND MACROCYCLES FOR SELF-ASSEMBLING OLIGOMERS AND MOLECULAR RECOGNITION VIA HYDROGEN BONDING
Maria Escamilla, Linda Gutierrez-Tunstad.
California State University Los Angeles, Los Angeles, CA.
Cavitands are molecules that have a bowl-like conformation that enables them to bind or entrap smaller compounds. The framework for our molecules is the resorcinarene macrocycle, which is very attractive due to its easily modifiable structure. The goal of our project is to synthesize biscavitands with different functional groups that can self-assemble via hydrogen bonding. We will be exploring how different functional groups such as hydroxyl and carboxylic acids will affect the formation of oligomers or capsules, as well as shape, size, and guest complexation. Poly-hydroxy and –carboxylic acid compounds are of great interest, because of their ability to mimic biological interactions. Similar macrocyles have been used in protein surface recognition, drug discovery, and biotechnology. A synthetic route encompassing organometallic chemistry has been used to develop a series of biscavitands that are polyfunctionalized with hydroxyl and/or carboxylic acids. Characterization of all compounds will be made by nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and infrared spectroscopy. Progress in physical studies will be reported, and we expect the hydrogen bonding network will influence the type of structures and functions observed for the biscavitands.