ArticleJournal of the American Chemical Society2013
Amphidynamic crystals of a steroidal bicyclo[2.2.2]octane rotor: a high symmetry group that rotates faster than smaller methyl and methoxy groups.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Engineering molecular rotor-stator ligand architectures on copper nanoclusters for efficient photothermal conversion.Nature communications · 2026Article
- Photoresponsive porous materials.Nanoscale advances · 2021Review
- Photoinduced Pedalo-Type Motion in an Azodicarboxamide-Based Molecular Switch.Angewandte Chemie (International ed. in English) · 2018Article
- Ultrafast rotation in an amphidynamic crystalline metal organic framework.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Artificial Molecular Machines.Chemical reviews · 2015Review
- Asymmetric 1,4-bis(ethynyl)bicyclo[2.2.2]octane rotators via monocarbinol functionalization. Ready access to polyrotors.Beilstein journal of organic chemistry · 2015Article
- Solid-State NMR-Assisted Dynamic Characterization of two Isostructural Solvates of 5α-Bromo-6β,19-Epoxy-Androstan-3β,17β-Diol Diacetate.Magnetic resonance in chemistry : MRCArticle
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3 authors.
Funding
Abstract
The synthesis, crystallization, single crystal X-ray structure, and solid state dynamics of molecular rotor 3 provided with a high symmetry order and relatively cylindrical bicyclo[2.2.2]octane (BCO) rotator linked to mestranol fragments were investigated in this work. By use of solid state (13)C NMR, three rotating fragments were identified within the molecule: the BCO, the C19 methoxy and the C18 methyl groups. To determine the dynamics of the BCO group in crystals of 3 by variable temperature (1)H spin-lattice relaxation (VT (1)H T1), we determined the (1)H T1 contributions from the methoxy group C19 by carrying out measurements with the methoxy-deuterated isotopologue rotor 3-d6. The contributions from the quaternary methyl group C18 were estimated by considering the differences between the VT (1)H T1 of mestranol 8 and methoxy-deuterated mestranol 8-d3. From these studies it was determined that the BCO rotator in 3 has an activation energy of only 1.15 kcal mol(-1), with a barrier for site exchange that is smaller than those of methyl (E(a) = 1.35 kcal mol(-1)) and methoxy groups (E(a) = 1.92 kcal mol(-1)), despite their smaller moments of inertia and surface areas.
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