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Synthesis of Fluorine‐Containing Molecular Rotors and Their Assembly on Gold Nanoparticles
Author(s) -
Thibeault Dominic,
Auger Michèle,
Morin JeanFrançois
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000252
Subject(s) - sonogashira coupling , chemistry , moiety , colloidal gold , molecule , nuclear magnetic resonance spectroscopy , spectroscopy , nanoparticle , linear molecular geometry , solid state nuclear magnetic resonance , molecular dynamics , fluorine , regioselectivity , combinatorial chemistry , nanotechnology , stereochemistry , organic chemistry , computational chemistry , catalysis , materials science , palladium , physics , nuclear magnetic resonance , quantum mechanics
A series of eight rotors containing thiol groups for attachment to gold surfaces and fluorine atoms for solid‐state 19 F NMR spectroscopy have been prepared through linear, multistep synthesis. The common rotating part of the rotors (rotator), consisting of a 2,6‐difluorobenzene moiety, is introduced into the rotor structure through an unusual regioselective Sonogashira coupling with 2,6‐difluoro‐1,4‐diiodobenzene. Rotors with different bulky trityl headgroups were prepared, along with their linear, less hindered analogues. These molecular rotors were assembled on gold nanoparticles (AuNPs) and preliminary characterization was performed on these AuNPs in order to study the effects of the sizes of the molecules on the packing behaviour on the AuNP surfaces. As expected, we found that linear molecules adopt more closely packed structures on the surfaces than their bulky analogues. This offers a very promising opportunity to study rotation dynamics at the molecular level by solid‐state NMR spectroscopy.