A novel fullerene lipoic acid derivative: Synthesis and preparation of self-assembled monolayers on gold

Viana, Ana S.; Leupold, S.; Eberle, Christoph; Shokati, Touraj; Montforts, Franz‐Peter; Abrantes, L.M.

doi:10.1016/j.susc.2007.09.011

Cited by 12 publications

(6 citation statements)

References 40 publications

(53 reference statements)

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“…Therefore, a thiol or any other sulfur-containing group grafted to the C 60 cage is expected to play a powerful role in directing the surface assembly of such fullerenes (Figure b). However, the majority of studies detailing thiol-functionalized fullerenes deposited on surfaces observe the formation of disordered structures. − The two examples of ordered fullerene SAMs reported (for alkylthiol- and anthrylphenylacetylenethiol-functionalized C 60 ) , show SAMs with very similar long-range geometry to the hcp arrays formed by unmodified C 60 .…”

Section: Introductionmentioning

confidence: 99%

Functionalized Fullerenes in Self-Assembled Monolayers

et al. 2011

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Anisotropy of intermolecular and molecule-substrate interactions holds the key to controlling the arrangement of fullerenes into 2D self-assembled monolayers (SAMs). The chemical reactivity of fullerenes allows functionalization of the carbon cages with sulfur-containing groups, thiols and thioethers, which facilitates the reliable adsorption of these molecules on gold substrates. A series of structurally related molecules, eight of which are new fullerene compounds, allows systematic investigation of the structural and functional parameters defining the geometry of fullerene SAMs. Scanning tunnelling microscopy (STM) measurements reveal that the chemical nature of the anchoring group appears to be crucial for the long-range order in fullerenes: the assembly of thiol-functionalized fullerenes is governed by strong molecule-surface interactions, which prohibit formation of ordered molecular arrays, while thioether-functionalized fullerenes, which have a weaker interaction with the surface than the thiols, form a variety of ordered 2D molecular arrays owing to noncovalent intermolecular interactions. A linear row of fullerene molecules is a recurring structural feature of the ordered SAMs, but the relative alignment and the spacing between the fullerene rows is strongly dependent on the size and shape of the spacer group linking the fullerene cage and the anchoring group. Careful control of the chemical functionality on the carbon cages enables positioning of fullerenes into at least four different packing arrangements, none of which have been observed before. Our new strategy for the controlled arrangement of fullerenes on surfaces at the molecular level will advance the development of practical applications for these nanomaterials.

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Section: Introductionmentioning

confidence: 99%

Functionalized Fullerenes in Self-Assembled Monolayers

et al. 2011

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“…Self-assembled monolayers of porphyrins are of particular interest since the orientation of the ring can be controlled [23]. For example, when using monothiolated and multithiolated porphyrins perpendicular and coplanar oriented porphyrin monolayers can be, respectively, obtained [24].…”

Section: Introductionmentioning

confidence: 99%

Dissolved oxygen amperometric sensor based on layer-by-layer assembly using host–guest supramolecular interactions

Damos

Luz

Tanaka

et al. 2010

Analytica Chimica Acta

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“…The redox potentials are close to the values reported for fullerene lipoic acid derivative or fullerene with long alkane thiol chain self-assembled on the gold substrates. 48,49 The peak currents increase linearly with scan rate as predicted for the surface immobilized species. The surface concentration of the deprotected ATF-C 60 derivative was calculated based on eqn (3):…”

Section: Application Of Deprotected Thioacetate Derivative Atf-c 60 F...mentioning

confidence: 58%

Fullerene modification of gold electrodes and gold nanoparticles based on application of aromatic thioacetate-functionalized C₆₀

et al. 2014

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A new procedure for the synthesis of S-acetyl-derivatized fullerene is described. The deprotected aromatic S-acetyl-derivatized fullerene was employed for efficient modification of gold electrode and gold nanoparticles. The proposed deposition procedure of fullerene derivative at Au surfaces allows the control of the thickness of the self-assembled fullerene layer. The modified surfaces were characterized by electrochemical methods and X-ray photoelectron spectroscopy (XPS). Functionalized fullerenes largely retain favorable redox electronic properties, behaving as an electron sink and revealing 4 reversible sequential 1e electrode processes at slightly more negative potentials than those observed for unsubstituted C 60 . For the first time, fullerene-capped gold nanoparticles were obtained by a two -step ligand exchange procedure involving substitution of alkanethiol with thiolated fullerene derivative following the synthesis of alkanethiol capped nanoparticles. The ligand exchange procedure was very efficient -the number of fullerene moieties per single gold nanoparticle was found to be as high as 30.

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A novel fullerene lipoic acid derivative: Synthesis and preparation of self-assembled monolayers on gold

Cited by 12 publications

References 40 publications

Functionalized Fullerenes in Self-Assembled Monolayers

Functionalized Fullerenes in Self-Assembled Monolayers

Dissolved oxygen amperometric sensor based on layer-by-layer assembly using host–guest supramolecular interactions

Fullerene modification of gold electrodes and gold nanoparticles based on application of aromatic thioacetate-functionalized C₆₀

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A novel fullerene lipoic acid derivative: Synthesis and preparation of self-assembled monolayers on gold

Cited by 12 publications

References 40 publications

Functionalized Fullerenes in Self-Assembled Monolayers

Functionalized Fullerenes in Self-Assembled Monolayers

Dissolved oxygen amperometric sensor based on layer-by-layer assembly using host–guest supramolecular interactions

Fullerene modification of gold electrodes and gold nanoparticles based on application of aromatic thioacetate-functionalized C60

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Fullerene modification of gold electrodes and gold nanoparticles based on application of aromatic thioacetate-functionalized C₆₀