Synthesis of differentially functionalized OPEs via regioselective deprotection for use in molecular electronics

ORGN 354

Kusum L. Chandra, klchandr@ncsu.edu and Christopher B. Gorman. Department of Chemistry, North Carolina State University, Raleigh, NC 27695
Oligo- and polymeric phenylene ethynylene molecules (OPEs) have drawn much attention due to their interesting optical, electrical, optoelectronic properties, and their interesting applications in optoelectronic devices such as molecular wires, molecular scale electronic devices, solar cells, light emitting diodes, and field-effect transistors. Though various syntheses of OPE's have been reported in the literature, there are still some challenging issues. Specifically, to bridge these molecules between multiple contacts with directional control we need to establish synthetic methods that allow two or more different functional groups, which in turn will allow orthogonal self assembly of the molecule. In this presentation, the relative efficiency of various differential deprotection strategies for terminal acetylenes will be illustrated and ideal conditions for incorporation of various end groups like thioacetate, isonitrile and carboxylic acids will be discussed.