Experimental and theoretical insights on the synthesis and electronic properties of oligothiophene sulfones

ORGN 601

Ted M. Pappenfus, pappe001@morris.umn.edu, Division of Science and Mathematics, University of Minnesota, Morris, 600 East Fourth Street, Morris, MN 56267 and Paul C. Ewbank, Department of Chemistry, Juniata College, 1700 Moore St., Huntingdon, PA 16652.
Oligothiophene sulfones (or S,S-dioxides) are an important class of organic materials for a variety of applications including opto-electronic devices and biodiagnostics. Previous work has shown that oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed, however, relative to oligomers without beta-alkyl substitution. This current work sheds additional light on this selectivity with the support of both experiment and theory. Insight into the electronic properties of the oxidized and parent oligomers has been explored with the use of density functional theory calculations. Preliminary data on analogous nine ring systems will also be reported.
 

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