International audienceThe chemistry of aryldiazonium salts has been thoroughly used in recent years to graft in a very simple and robust way ultrathin polyphenylene-like films on a broad range of surfaces. We show here that the same chemistry can be used to obtain self-adhesive surfaces. This target was reached in a simple way by coating various surfaces with chemisorbed organic films containing active aryldiazonium salts. These self-adhesive surfaces are then put into contact with various species (molecules, polymers, nanoparticles, nanotubes, graphene flakes, etc.) that react either spontaneously or under activation with the immobilized aryldiazonium salts. Our self-adhesive surfaces were synthesized following a simple aqueous two-step protocol based on p-phenylenediamine diazotisation. The first diazotisation step results in the robust grafting of thin polyaminophenylene (PAP) layers onto the surface. The second diazotisation step changed the grafted PAP film into a poly-aryldiazonium polymer (PDP) film. The covalent grafting between those self-adhesive surfaces and the target species was achieved by direct contact or by immersion of the self-adhesive surfaces in solution. We present in this preliminary work the grafting of multi-wall carbon nanotubes (MWCNTs), flakes of highly oriented pyrolytic graphite (HOPG), various organic compounds and copper nanoparticles. We also tested these immobilized aryldiazonium salts as electropolymerization initiators for the grafting-to process
Organic ligands containing the chelating carbodithioate group are excellent candidates for the surface functionalization of various semiconductor and metal nanoparticles or flat substrates. We provide a simple synthetic scheme for the preparation of a series of regioregular oligo- and polythiophenes containing this functional group. In the first step, 3-[4-(bromomethyl)phenyl]-2,5-dibromothiophene is coupled either to 3-n-octylthiophene or to 3,3‘ ‘-dioctyl-2,2‘:5‘,2‘ ‘-terthiophene, leading to quasisymmetric thiophene trimers or heptamers, respectively. In the second step, these oligomers are submitted to oxidative polymerization, and finally the carbodithioic acid function is introduced. This procedure can be generalized for the preparation of a large number of functional oligo- and polythiophenes by simply varying the chemical structure of the thiophene precursors used. We illustrate the grafting of these compounds on the surface of CdSe nanocrystals with the example of 4-thiophen-3-yldithiobenzoic acid. Spectroscopic studies of the resulting thiophene-functionalized nanocrystals reveal photoinduced charge transfer at the organic/inorganic interface.
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