Synthesis of Unsymmetrical Triarylamines for Photonic Applications via One-Pot Palladium-Catalyzed Aminations

Creators: Thayumanavan, S.; Barlow, Stephen; Marder, Seth R.

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Abstract

Syntheses of unsymmetrically substituted triarylamines have been achieved by a one-pot procedure using C−N bond-forming reactions, where two aryl bromides are sequentially added to an arylamine in the presence of a palladium catalyst. This methodology has been utilized to synthesize a number of substituted analogs of 4,4'-bis(m-tolylphenylamino)biphenyl, which may be useful as the hole transport component of vapor-deposited organic light-emitting diodes. The variations in the substitution are anticipated to lead to a variety of band gaps, band offsets, and glass transition temperatures in this class of materials.

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© 1997 American Chemical Society. Received August 13, 1997. The work in this paper was performed in part at the Center for Space Microelectronics Technology, Jet Propulsion Laboratory (JPL), California Institute of Technology under contract with the National Aeronautics and Space Administration (NASA). The work was sponsored by the Ballistic Missile Defense Organization, Innovative Science and Technology Office. In addition the work was supported by the U.S. Office of Naval Research (ONR) through the MURI Center for Advanced Multifunctional Nonlinear Optical Polymers and Molecular Assemblies (CAMP), the U.S. National Science Foundation (NSF), a MRSEC of the National Science Foundation (DMR-94-00362), and the USAF Office of Scientific Research (AFOSR). We thank Professor N. R. Armstrong (University of Arizona) for valuable discussions.

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