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08:40
Light-driven Molecular Motors on Surfaces for Single Molecular Imaging
Published on: March 13, 2019
Progress toward a rationally designed, chemically powered rotary molecular motor
T Ross Kelly1, Xiaolu Cai, Fehmi Damkaci
1E. F. Merkert Chemistry Center, Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Journal of the American Chemical Society
|January 11, 2007
Summary
Researchers aimed for repeated unidirectional rotation in a molecular machine using compound 7. However, intramolecular urethane formation, crucial for rotation, did not occur, hindering progress in molecular machinery.
Area of Science:
- Molecular machinery
- Supramolecular chemistry
- Organic synthesis
Background:
- Prototype 1 demonstrated 120 degrees of unidirectional rotation powered by phosgene.
- Triptycene-based molecular machines offer potential for controlled motion.
Purpose of the Study:
- To design and synthesize compound 7 for repeated unidirectional rotation.
- To investigate the mechanism of phosgene-induced rotation in a triptycene derivative.
Main Methods:
- Synthesis of compound 7 involving benzyne addition, stilbene photocyclization, and Stille coupling.
- Utilized 4-(dimethylamino)pyridine (DMAP) for selective phosgene delivery.
- Investigated intramolecular urethane formation via 1,1'-carbonyldiimidazole.
Main Results:
- Compound 7 was successfully synthesized with DMAP for selective phosgene relay.
- The DMAP unit regioselectively relayed 1,1'-carbonyldiimidazole, but not phosgene.
- Triptycene rotation did not occur, and intramolecular urethane formation was unsuccessful.
Conclusions:
- The designed intramolecular urethane formation pathway failed in compound 7.
- Potential reasons for failure include hydrogen bonding or Bürgi-Dunitz interactions involving DMAP.
- Further research is needed to overcome conformational barriers in triptycene-based molecular machines.
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