Synthesis and characterization of 2,6-disubstituted benzobisazoles: New building blocks for conjugated materials

ORGN 224

Malika Jeffries-El, Jared F. Mike, jfmike@iastate.edu, Jeremy J. Intemann, jeremyi@iastate.edu, and Andrew J. Makowski, makowski@iastate.edu. Department of Chemistry, Iowa State University, 1605 Gilman Hall, Ames, IA 50011

Polybenzobisazoles posses many exceptional electronic, optical and thermal properties and thus are well suited for organic semiconducting applications, yet these materials have found limited utility due their poor solubility in organic solvents. A promising approach for the synthesis of soluble materials is the combination of the benzobisazole moiety with substituted aromatic rings. However, the harsh conditions required for the synthesis of benzobisazoles has prevented functionalization bearing reactive handles. Our group has developed a new approach for the synthesis of functional benzo[1,2-d;4,5-d'] bisoxazole (trans-BBO), benzo[1,2-d;5,4-d'] bisoxazoles (cis-BBO) and benzo[1,2-d;4,5-d'] bisthiazole (trans-BBZT), via the Lewis acid catalyzed reaction of various orthoesters with corresponding diamino diols and dithiols respectively. In all cases the target compounds were obtained cleanly and in high yield. Subsequent transformations yield several building blocks suitable for coupling with various aryl compounds via a number of methods. The utility of these compounds for synthesizing new conjugated polymers will be demonstrated.

 

Young Academic Investigators
8:00 AM-12:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- 207A, Oral

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009