ORGN 360 |
| This work presents the successful synthesis of molecular gyroscope 1, analogous in shape to a macroscopic gyroscope, with a freely rotating mass and an encapsulating frame. The molecular structure consists of a rigid frame composed of triarylmethyl groups (in blue), which encapsulate a 1,4-diethynylbenzene rotator (in red). These compounds are designed to sustain free rotation in the solid state by preventing steric interactions within close neighbors in the crystal lattice. Initial attempts to synthesize 1 through alkylation of a hexa-phenol precursor led to structure 2, with a topology that consists of one meridional (north-south) and two zonal (east-west) bridges. Therefore, we set out to synthesize 1 by a toposelective scheme based on the Pd(0)-catalyzed of coupling of 4-[3,3,3-tri-(meta-ω-bromodecyloxyphenyl)propynyl]iodobenzene and 3,3,3-tri-(meta-hydroxyphenyl)propyne. Subsequent exposure of the asymmetric structure to basic media led to the fully-bridged gyroscope 1 with a tri-meridional topology. The synthesis, structures, and properties of these compounds will be analyzed in detail.
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Materials, Devices, and Switches
1:00 PM-4:40 PM, Monday, August 20, 2007 BCEC -- 258A, Oral
Division of Organic Chemistry |
