Paper
3-Aryl-3-(trifluoromethyl)diazirines as Versatile Photoactivated “Linker” Molecules for the Improved Covalent Modification of Graphitic and Carbon Nanotube Surfaces
Published Jul 26, 2011 · Elliot Lawrence, Gregory Wildgoose, L. Aldous
Chemistry of Materials
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Abstract
3-Aryl-3-(trifluoromethyl)diazirines are shown to be synthetically useful photoactivated carbene precursors that can be used as molecular “tethers” to facilitate the improved covalent surface modification of graphitic carbon and carbon nanotubes with a potentially large variety of chemical species. Proof-of-concept is demonstrated by the synthesis, as well as spectroscopic and electrochemical characterization, followed by photoactivated attachment of the organometallic diazirine derivative, 3-[3-(trifluoromethyl)diazirin-3-yl]phenyl ferrocene monocarboxylate, to the surface of vitreous carbon, and also to two different morphologies of multiwalled carbon nanotubes (“bamboo-like” and “hollow-tube”, denoted as b-MWCNTs and h-MWCNTs, respectively). The latter differ only in the relative amounts of “edge-plane-like” defect sites (at the termini of the nanotubes) and “basal-plane-like” pristine sidewall regions. The facile covalent coupling of the ferrocenyl “probe” moiety to the diazirine “linker” was confirme...
3-Aryl-3-(trifluoromethyl)diazirines serve as versatile photoactivated "tethers" for improved covalent surface modification of graphitic carbon and carbon nanotubes with a variety of chemical species.
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