ORGN 498 |
| Several iminocyclobutane compounds have been previously synthesized and found to possess many interesting properties. In particular, orbital interactions in these compounds occur via two pathways, across the ring (transannular) and around the ring (circumannular). By varying the ring substituents, the effect of the circumannular interaction on the free energy of inversion of groups attached to nitrogen were determined using variable temperature NMR. Understanding the basic properties of this ring system is necessary in order to design the synthesis of novel compounds with the potential for use as molecular wires, electronic switches, conductive monomers, and conductive polymers. Furthermore, the effect of symmetric (bis) and asymmetric (mono) addition of larger aromatic groups, to the iminocyclobutane ring via Suzuki coupling, was used as a pathway to yield larger conjugated systems, a prerequisite for the application of such a system as a material targeted for OLED applications. The resulting compounds were characterized by spectral techniques in order to measure the extent of circumannular and transannular interaction. R = R'= naphthyl, phenyl, p-bromophenyl
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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 |
