Phenylethyloxacalixarene Synthesis Via TBS- Protected Phenylethynylcatechols

Abstract

The purpose of this work is to develop a method to synthesize annulene- o,m,o,moxacalix[4]arene hybrids. These molecules are expected to adopt a conformation where the annulenes are in a close, cofacial orientation, resembling a tweezer. Once prepared, these hybrids will provide insights into the interactions between cofacial aromatic and antiaromatic systems. To develop the methodology for the synthesis of these annulene-oxacalixarene hybrids, a series p- substituted phenylethynyl- o,m,o,m-oxacalix[4]arenes is being prepared. The substituents range from strongly electron withdrawing to strongly electron donating, allowing a systematic study of the electronic nature of the phenylethynyloxacalixarenes and providing experience on how to synthesize and purify annulene compounds. This poster will discuss our progress in the preparation of the phyenyethynyloxacalixarene series.