ORGN 587 |
| Electron-rich triarylamines are important building blocks for a number of materials used in nonlinear optical applications involving two-photon absorption (2PA), electro-optic activity, and third-harmonic generation. In addition, bis(triarylamine)s are widely used as hole-transport materials for applications including xerography, organic light-emitting diodes, and photorefractives. The palladium-catalyzed amination reaction of aryl-halides with a large variety of amine substrates has been extensively investigated in recent years. Recently, microwave-assisted synthesis has been applied successfully in many fields of synthetic organic chemistry, including palladium-catalyzed aminations; however, we found no reports use microwave heating to synthesize electron-rich triarylamines. We have been able to use microwave heating to assist in the synthesis of new electron-rich bis(diarylamino)thiophene-based materials from diarylamines and 2-bromothiophene derivatives. In most cases, we improved the yields and decreased the times required for the reactions relative to conventional conditions, and in some cases, we also decreased the number and amounts of byproducts formed. Systems that will be presented here include bis(diarylamine) derivatives of dithienothiophene and dithienylethylene as well as a new functionalized monomer and subsequent polymers formed from a dithienopyrrole derivative.
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
