ORGN 272 |
| Andrew B Holmes1, Joseph Frey1, Steffen Proemmel1, Kai Siegenthaler1, and Andrew D Bond2. (1) Melville Laboratory, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom, (2) Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom |
| Dithienothiophene is an attractive condensed sulfur heterocycle for the preparation of high charge mobility materials, and has potential as the active layer in field effect transistors. The published syntheses of this compound have all suffered from weaknesses in one of the ring closure steps. It is now shown that a simple annelation of 2,5-diformyl-3,4-dibromothiophene produces dithienothiophene derivatives in excellent yield. The process can be modified to include the corresponding 2,5-diacylthiophenes, and enables unsymmetrical derivatives to be prepared with ease. Directed metallation procedures offer access to various substituted dithienothiophene derivatives for organometallic cross coupling polycondensations. In this paper the synthetic procedures and device properties will be reported. |
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Functional pi-Electronic Systems
8:30 AM-12:00 PM, Monday, March 24, 2003 Convention Center -- Room 353-355, Oral
Division of Organic Chemistry |