Nanodragster shows progress to Better Molecular Machines

Previously nanocars were created and now there is a somewhat faster nanodragster. The Nanodragster operates at lower temperatures and rolls more easily. It was created by James Tour and his research colleagues.

The synthesis and imaging by scanning tunneling microscopy of a mixed wheeled nanovehicle composed of a p-carborane small-wheeled short front axle and a C60 large-wheeled long rear axle that has been termed a nanodragster due to the structural relation to a dragster are reported. This nanodragster is expected to exhibit motion at a lower temperature than pure C60-wheeled nanocars and should allow the investigation of the role played by p-carborane wheels in directional motion.

28 page pdf with supplemental information on Molecular Machinery: Synthesis of a “Nanodragster”

General Synthetic Methods. 1H NMR and 13C NMR spectra were recorded at 400 and 500 MHz, respectively, on a Bruker Avance 400 and Avance 500 spectrometer. Proton chemical shifts (δ) are reported in ppm downfield from tetramethylsilane (TMS). Mass spectroscopy was performed at the Rice University Mass Spectrometry Laboratory or at the University of South Carolina Mass Spectrometry Laboratory. IR spectra were obtained on a Nicolet Avatar 360 FTIR. All Reagent grade tetrahydrofuran (THF) and diethyl ether (Et2O) were distilled under nitrogen over sodium benzophenone ketyl. Triethylamine and CH2Cl2 were distilled over CaH2 under nitrogen unless otherwise stated. THF and triethylamine were well-degassed with a stream of argon for 1 h before being used in the Castro-Stephens-Sonogashira coupling. All other reagents were purchased from commercial suppliers and used without further purification. Trimethylsilylacetylene (TMSA) was donated by FAR Research Inc. or Petra Research Inc. Flash chromatography was carried out using silica gel (230-400 mesh from EM science). Thin layer chromatography (TLC) was carried out on glass plates coated with silica gel 40 F254 purchased from EM Science. All reactions were conducted under a dry oxygen-free atmosphere using oven-dried glassware unless otherwise stated. PdCl2(PPh3)2,1 2,2 33, 73 and 92 were prepared using literature procedures.

* General Procedure for the Coupling of a Terminal Alkyne with an Aryl Halide Using a Palladium-Catalyzed Sonogashira Coupling.

* General procedure for the removal of TMS/TIPS protecting groups.

* Spectra for Compounds