Two Synthetic Approaches to the Formation of Oxacalixarene-Annulene Hybrid Molecules

Abstract

The purpose of this work is to synthesize annulene-o,m,o,m-oxacalix[4]arene hybrid molecules which exist in a tweezer-like conformation with cofacial annulenes due to the chalice-like nature of oxacalixarenes. These hybrid molecules will provide insight on interactions between cofacial aromatic and antiaromatic annulenes. To develop the methodology for the synthesis of these annulene-oxacalixarene hybrids, a series p-substituted phenylethynyl-o,m,o,m-oxacalix[4]arenes are being prepared. This poster will discuss two different approaches to the synthesis of these compounds. In the first method, the Sonogashira coupling precedes oxacalixarene formation. In the second approach, a tetraiodo oxacalixarene undergoes Sonogashira coupling with appropriate phenylacetylenes.