Synthesis of novel thieno[3,4-b]pyrazine-based building blocks as precursors to low band gap conjugated polymers

ORGN 500

LI Wen, Li.wen@ndsu.edu, Jon P. Nietfeld, jon.nietfeld@ndsu.edu, Chad M. Amb, chad.amb@ndsu.edu, and Seth C. Rasmussen, seth.rasmussen@ndsu.edu. Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, ND 58105
One approach to tuning the properties of conjugated polymers is the annulation of aromatic rings to the polymeric repeat units, resulting in a powerful approach to the production of low band gap materials. Thieno[3,4-b]pyrazines are an excellent example of such a fused-ring building block and these units have been utilized to produce a wide variety of low band gap systems. However, 2,3-difunctionalized thieno[3,4-b]pyrazines have been currently limited to either the dialkyl or diaryl analogues. In order to significantly expand the current family of thieno[3,4-b]pyrazines, we report herein the synthesis of new analogues containing electron-donating and electron-withdrawing groups as potential polymer precursors for low band gap materials. Synthetic details of the new series of thieno[3,4-b]pyrazines will be presented, along with optical and electrochemical characterization of the resulting species. The tuning effects of the new side chains on both the properties of the precursors and potential new polymeric materials will be discussed.
 

Materials, Devices and Switches
1:00 PM-4:40 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Nouvelle, Blrm. C, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008