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Related Experiment Video

Updated: Jul 17, 2026

Light-driven Molecular Motors on Surfaces for Single Molecular Imaging
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
PubMed
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.

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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.