ORGN 496 |
| α,α-Hexithiophene and its derivatives have attracted widespread interest in recent years not only as a model for polythiophene but also in their own right as a versatile electronically active component in electronic devices such as field-effect transistors, OLEDs, molecular wires and photovoltaic cells. Although considerable control over electronic properties can be achieved through synthetic modification, post-synthetic tuning of properties by external stimuli, specifically light, by incorporation of a photo-responsive unit is challenging due to the ability of oligothiophenes to quench electronically excited states efficiently. In this present study, we describe the synthesis and physical properties of two α,α-hexithiophene compounds (1 and 2), which incorporate photoswitchable dithienylhexafluorocyclopentene units; units that have attracted considerable attention in optoelectronic memory and display devices in recent years due to their fatigue-resistance and excellent thermal stability. The systems prepared show that the photochromic properties of the dithienylcyclopentene units can be retained even when attached directly to the hexithiophene ‘molecular wire'. 1. D. Fichou. Handbook of oligo- and polythiophenes; Wiley-VCH: Weinheim, 1999 2. F. Garnier. Acc. Chem. Res. 1999, 32, 209 3. F. Garnier, R. Hajlaoui, A. Yassar, P. Sruvastava. Science, 1994, 265, 1684 4. J. Nishida, T. Miyagawa, Y. Yamashita. Org. Lett., 2004, 6, 2523 5. W. A. Gazotti, A. F. Nogueira, E. M. Girotto, L. Micaroni, M. Martini, S. das Neves, M. –A. De Paoli. Handbook of Advanced Electronic and Photonic Materials and Devices ; H. S. Nalwa Ed ; Acadamic Press : San Diego, CA, 2001 6. a) M. Irie. Chem. Rev. 2000, 100, 1685 b) B. L. Feringa, Molecular Switches, Wiley VCH, Weinheim, 2001 c) H. Tian, S. J. Yang Chem. Soc. Rev. 2004, 33, 85 |
|
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 |