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Journal ArticleDOI

En route to surface-bound electric field-driven molecular motors.

Huahua Jian, +1 more
- 22 May 2003 - 
- Vol. 68, Iss: 13, pp 5091-5103
TLDR
Four caltrop-shaped molecules that might be useful as surface-bound electric field-driven molecular motors have been synthesized and Ellipsometric studies show that self-assembled monolayers of the caltrops are formed on Au surfaces with molecular thicknesses consistent with the desired upright-shaft arrangement.
Abstract
Four caltrop-shaped molecules that might be useful as surface-bound electric field-driven molecular motors have been synthesized. The caltrops are comprised of a pair of electron donor-acceptor arms and a tripod base. The molecular arms are based on a carbazole or oligo(phenylene ethynylene) core with a strong net dipole. The tripod base uses a silicon atom as its core. The legs of the tripod bear sulfur-tipped bonding units, as acetyl-protected benzylic thiols, for bonding to a gold surface. The geometry of the tripod base allows the caltrop to project upward from a metallic surface after self-assembly. Ellipsometric studies show that self-assembled monolayers of the caltrops are formed on Au surfaces with molecular thicknesses consistent with the desired upright-shaft arrangement. As a result, the zwitterionic molecular arms might be controllable when electric fields are applied around the caltrops, thereby constituting field-driven motors.

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Citations
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The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry†

TL;DR: Transition-Metal-Free Reactions, Alkynylation of Heterocycles, and Synthesis of Electronic and Electrooptical Molecules: A Review.
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TL;DR: The latest generations of sophisticated synthetic molecular machine systems in which the controlled motion of subcomponents is used to perform complex tasks are discussed, paving the way to applications and the realization of a new era of “molecular nanotechnology”.
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Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.

TL;DR: Coupling reaction of electron-deficient aryl bromides with imidazole or pyrazole occurs at 60-90 degrees C to provide the corresponding N-aryl products in good to excellent yields and the possible action of amino acids in these coupling reactions is discussed.
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