Synthesis Of The Monomeric Precursors Of A Clar Helicene And An Ortho-Helicene

Abstract

The aim of this project was to develop a synthesis for 2,3-dibromo-l,4divinylnaphthalene (the "elar helicene monomer") and for 1,2-dihexyl-4,5-diiodo3,6- divinylbenzene (the "o-helicene monomer,,).1,2 These monomers represent precursors of two ortho-helicenes, which are carbon nanostructures that are potentially useful to the development of computing technologies.3,4 The precursors were designed to be able to polymerize into helicenes by a method of molecular coupling and olefm metathesis. The elar helicene monomer was synthesized in relatively high yield (38% overall yield) and was fully characterized; however, deactivating features of the o-helicene monomer prevented a successful synthesis, though insights were gained that may aid the development of future techniques for similar projects.