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Molecular Spur Gears with Triptycene Rotators and a Norbornane-Based Stator

Xing Jiang, Song Yang, Marcus J. Jellen, K. N. Houk, Miguel A. Garcı́a-Garibay

2020Organic Letters21 citationsDOI

Abstract

We report efforts to prepare a molecular spur gear utilizing a convenient synthesis of a norbornane stator that positions two interdigitated diyne-linked triptycenes in parallel alignment. While gearing was not observed by 19F NMR for a −CF3-labeled analog at temperatures as low as 213 K, we used molecular dynamics simulation and 2D metadynamics calculations to understand the gearing/slippage energetic profile for various molecular spur gears to guide future designs of these systems.

Topics & Concepts

NorbornaneMetadynamicsSlippageChemistrySpurMolecular dynamicsStatorSpur gearTriptyceneComputational chemistryStereochemistryMechanical engineeringOrganic chemistryEngineeringStructural engineeringSupramolecular Chemistry and ComplexesMolecular Junctions and NanostructuresForce Microscopy Techniques and Applications
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