ORGN 69 |
| Polar order is central to a variety of solid state properties and it has been very hard to achieve. It has been our aim to develop a rational design for crystals of molecular organic materials with very high dipole-parallel alignment. Our approach involves the use of arene-arene interactions as lateral synthons to overcome the intrinsic dipole-dipole repulsions with quadrupole-quadrupole interactions. We have demonstrated near-perfect and perfect dipole-parallel alignment in crystals of the azines X-C6H4-CR=N-N=CR-C6H4-Y (R=H,Me; X=MeO; Y=Hal). We are now exploring the corresponding butadiene derivatives X-C6H4-CR=CH-CH=CR-C6H4-Y (R=H,Me). Here we will compare the parent azines to the corresponding butadienes. The synthesis of 2,5-diphenyl-2,4-hexadiene is not trivial but was accomplished with DMPU. Without DMPU, the Horner-Emmons reaction yields 1-methyl-1,3,6-triphenyl-7-(2-phenyl-propenyl)-1,2-dihydro-naphthalene and its formation is rationalized.
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Materials, Devices, and Switches
1:00 PM-5:00 PM, Sunday, 13 March 2005 Convention Center -- Room 9, Oral
Division of Organic Chemistry |
