SYNTHESIS OF HETEROFUNCTIONALIZED HEXAARYLBENZENES

Washington University, Saint Louis MO

Investigators

Linked publications & trials

Abstract

This subproject is one of many research subprojects utilizing the resources provided by a Center grant funded by NIH/NCRR. The subproject and investigator (PI) may have received primary funding from another NIH source, and thus could be represented in other CRISP entries. The institution listed is for the Center, which is not necessarily the institution for the investigator. We are interested in the construction of novel extended conjugated systems capable of being incorporated into useful opticoelectronic materials for such devices as heterojunction organic photovoltaics, conductive or semiconductive materials, and organic light-emitting diodes. Our synthetic approach involves easily synthesized oligomer and polymer precursors that can be reacted further to create polyaromatic networks. A phenomenon that we would like to exploit is the transfer of conformational information in the polymeric precursor- a folded structure for instance- to long-range structural order in the product material. Two examples of such systems are pictured below: a zipper polymerization of oligo(o-phenylene ethynylene) to provide long, soluble, graphitic ribbons, and a synthetic target of short buckytube-like graphitic belts. We are also interested in the construction of suitable components for self-assembling non-covalent dynamic combinatorial libraries of folding chain molecules. Nature has evolved very efficient catalytic and information-storing systems consisting of folded oligomers, namely proteins and nucleic acids. Our ultimate goal is progress towards identifying synthetic chain molecules that serve as efficient protein mimics, in their ability to fold to unique structures, to bind small molecules, and in the best-case scenario to catalyze small molecule reactions. This endeavor involves screening a large number of possible monomer backbones and chain sequences. Dynamic combinatorial libraries allow these chains to be targeted towards folding into specific conformations that are strong, specific binders of small molecules.