ORGN 654 |
| The new nonlinear optical chromophores 2-[4-[2-(4-pyridinyl)ethenyl]phenoxy]phenol (1), N-methyl-5-[2-(4-pyridinyl)ethenyl]-1H-pyrrole-2-carboxaldehyde-4-iodoperfluorophenylhydrazone (2), and N-methyl-5-[2-(4-pyridinyl)ethenyl]-1H-pyrrole-2-carboxaldehyde-methy-4-iodoperfluorophenylhydrazone (3) designed to provide a polar halogen-bonding network have been synthesized and characterized. Single crystal data confirms that 1 molecules interact via a strong head-to-tail N-I-C halogen bonding. Films of chromophore 1 and 3 can be conveniently fabricated via physical vapor deposition. Second-harmonic generation measurements demonstrate for the first time that the vapor-deposited films exhibit a net polar alignment of the molecular dipoles driven by molecular halogen-bonding interactions. The nonlinear optical coefficient (c332 of ~ 7 pm/V) and IR transparency of 3 demonstrate the potential of this technique for the fabrication of EO-active materials.
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Materials, Devices, and Switches
1:00 PM-5:00 PM, Thursday, 30 March 2006 Georgia World Congress Center -- Georgia Ballroom 2, Oral
Division of Organic Chemistry |
