Electronic properties of oligothiohenes with ring fusion

ORGN 595

John T. Henssler, henssler@umich.edu1, Xinnan Zhang, xinnanz@umich.edu2, and Adam J Matzger, matzger@umich.edu2. (1) Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, (2) Department of Chemistry and Macromolecular Science and Engineering, University of Michigan, 930 N. University, Ann Arbor, MI 48109-1055
Employing ring fusion in the production of novel oligomeric and polymeric conjugated thiophene materials has recently been revealed as a powerful approach to control properties. In cases where fused units are employed with more conventional oligothiophene segments, new regiochemical issues arise and developing an understanding of the interaction between subunits is desirable. Because only isolated examples of longer oligothiophenes (n>4) with ring fusion have been studied, trends in oligomers with more relevant conjugation lengths have yet to be investigated. In the present study, through Stille coupling reactions a series of fused-ring analogs of sexithiophene were produced (Scheme 1). The effects of extent and position of ring-fusion were analyzed by UV-vis and fluorescence spectroscopy to assess the resulting trends in conjugation and molecular conformation. To facilitate production of these oligomers an optimized synthesis of thieno[3,2-b]thiophene was devised that offers advantages in yield and purification efficiency over current procedures.

 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

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