Journal
TETRAHEDRON
Volume 64, Issue 36, Pages 8336-8345Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.05.143
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Funding
- NSF [DMR0605688, CHE0513503]
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We report the design, synthesis, thermal properties, and dynamic NMR characterization of four new molecular dirotors, each containing two rotary 1,4-diethynyl phenylene units, a bridging 1,3-bis(diphenylmethyl) benzene stator, and two capping triphenylmethyl groups. These compounds are variations of the well-known wheel and axle structures. Ambient temperature quadrupolar echo H-2 NMR spectra of phenylene-deuterated samples revealed line shapes consistent with dynamic processes having exchange rates > 10(8) s(-1), and more than the two minima typically observed for most phenylene rotators. Reasonable line-shape simulations were obtained with a model that involves four minima related by angular displacements of 0 degrees, 30 degrees, 180 degrees, and 230 degrees. Cooling the samples to 260 K revealed spectra consistent with samples that contain two or more components. These results indicate that novel wheel and axle structures do create a certain amount of free volume that allows for the desired mobility of the rotating units. (C) 2008 Elsevier Ltd. All rights reserved.
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