Synthesizing and Comparing a Series of Biscavitand Model Systems for Self-Assembling Oligomers

This study involves the development of synthetic macromolecules for self-assembling oligomers and as potential agents for biomolecular surface recognition. Resorcin[4]arene cavitands, molecular containers with well-defined dimensions and enforced cavities, are attractive scaffolds for the construction of synthetic macromolecules. Side to side biscavitands and the scope of their self-assembling and molecular recognition properties are relatively unknown. Our research aims to synthesize and analyze side to side biscavitands. A versatile synthetic design for generating biscavitands has been developed to incorporate functionalization at specific locations on the resorcin[4]arene framework for self-assembly. Compounds were characterized by nuclear magnetic resonance and ultraviolet-visible spectroscopy. We are generating a series of biscavitands of varying rigidity to compare to analogous flexible systems. Further, we are investigating synthetic sequences to the biscavitands to incorporate the essential functionality for self-assembly. We expect to observe self-assembling features on our side to side biscavitands and potential formation of oligomers. By understanding the self-assembling properties of our biscavitand systems, more elaborate molecules can be designed for biomolecular surface recognition.