Binding of fullerene C60 to gold surface functionalized by self-assembled monolayers of 8-amino-1-octane thiol: a structure elucidation.
TL;DR: The formation of self-assembled chemisorbed monolayers (SAM) of 8-amino-1-undecane thiol functionalized with fullerene C(60) on gold, has been studied by contact angle measurements, Fourier transform infrared-attenuated total reflection (FTIR-ATR), and X-ray photoelectron spectroscopy.
About: This article is published in Journal of Colloid and Interface Science.The article was published on 2003-12-01. It has received 50 citations till now. The article focuses on the topics: Chemical binding & Fullerene.
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432 citations
TL;DR: This work designed and synthesized several fullerene derivatives based on thiols, thiol acetates, and disulfides to address the characterization requirements, and these are described and delineated.
Abstract: The widely employed approach to self-assembly of fullerene derivatives on gold can be complicated due to multilayer formations and head-to-tail assemblies resulting from the strong fullerene−fullerene and fullerene−gold interactions. These anomalies were not examined in detail in previous studies on fullerene self-assembled monolayers (SAMs) but were clearly detected in the present work using surface characterization techniques including ellipsometry, cyclic voltammetry (CV), and X-ray photoelectron spectroscopy (XPS). This is the first time that SAMs prepared from fullerene derivatives of thiols/thiol esters/disulfides have been analyzed in detail, and the complications due to multilayer formations and head-to-tail assemblies were revealed. Specifically, we designed and synthesized several fullerene derivatives based on thiols, thiol acetates, and disulfides to address the characterization requirements, and these are described and delineated. These studies specifically address the need to properly charac...
89 citations
TL;DR: A new concept of the surface-segregated monolayer provides a facile and versatile approach to modifying the surface of organic semiconductors and is applicable to various organic optoelectronic devices.
Abstract: We report a new type of ordered monolayer for the surface modification of organic semiconductors. Fullerene derivatives with fluorocarbon chains ([6,6]-phenyl-C61-buryric acid 1H,1H-perfluoro-1-alkyl ester or FCn) spontaneously segregated as a monolayer on the surface of a [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) film during a spin-coating process from the mixture solutions, as confirmed by X-ray photoelectron spectroscopy (XPS). Ultraviolet photoelectron spectroscopy (UPS) showed the shift of ionization potentials (IPs) depending on the fluorocarbon chain length, indicating the formation of surface dipole moments. Surface-sensitive vibrational spectroscopy, sum frequency generation (SFG) revealed the ordered molecular orientations of the C60 moiety in the surface FCn layers. The intensity of the SFG signals from FCn on the surface showed a clear odd−even effect when the length of the fluorocarbon chain was changed. This new concept of the surface-segregated monolayer provides a facile and versat...
81 citations
TL;DR: A cell culture and migration study of glioma C6, MKN-45, MCF-7, and HepG-2 cells revealed that the polysaccharide-modified PDMS greatly improved the cytocompatibility of native PDMS.
Abstract: An improved approach for the surface modification of poly(dimethylsiloxane) (PDMS) using carboxymethyl cellulose (CMC), carboxymethyl β-1,3-dextran (CMD), and alginic acid (AA) was investigated. The PDMS substrates were first oxidized in a H2SO4/H2O2 solution to transform the Si−CH3 groups on their surfaces into Si−OH groups. Then methacrylate groups were grafted onto the substrates through a silanization reaction using 3-(trimethoxysilyl)propyl methacrylate. Sequentially, cysteamine was conjugated onto the silanized surfaces by the reaction between the thiol and methacrylate groups under 254 nm UV exposure. Afterward, the amino-terminated PDMS substrates were sequentially reacted with CMC, CMD, and AA in the presence of N-hydroxysuccinimide and 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide, resulting in the grafting of polysaccharides onto PDMS surfaces. The composition and chemical state of the modified surfaces were characterized by X-ray photoelectron spectroscopy (XPS). In addition, the stability a...
68 citations
TL;DR: The ability to guide pattern formation in films thick enough to be of interest for actual device applications (up to 200 nm in thickness) using feature sizes as small as 100 nm is demonstrated.
Abstract: We study the effects of patterned surface chemistry on the microscale and nanoscale morphology of solution-processed donor/acceptor polymer-blend films. Focusing on combinations of interest in polymer solar cells, we demonstrate that patterned surface chemistry can be used to tailor the film morphology of blends of semiconducting polymers such as poly-[2-(3,7-dimethyloctyloxy)-5-methoxy-p-phenylenevinylene] (MDMO-PPV), poly-3-hexylthiophene (P3HT), poly[(9,9-dioctylflorenyl-2,7-diyl)-co-benzothiadiazole)] (F8BT), and poly(9,9-dioctylfluorene-co-bis-N,N′-(4-butylphenyl)-bis-N,N′-phenyl-1,4-phenylendiamine) (PFB) with the fullerene derivative, [6,6]-phenyl-C61-butyric acid methyl ester (PCBM). We present a method for generating patterned, fullerene-terminated monolayers on gold surfaces and use microcontact printing and Dip-Pen Nanolithography (DPN) to pattern alkanethiols with both micro- and nanoscale features. After patterning with fullerenes and other functional groups, we backfill the rest of the surfa...
62 citations
References
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TL;DR: In this article, the results of photoelectric cross-sections for the Kα lines of magnesium at 1254 eV and of aluminum at 1487 eV were given for Z values up to 96.
4,891 citations
TL;DR: In this paper, the authors used contact angles and optical ellipsometry to study the kinetics of adsorption of monolayer films and to examine the experimental conditions necessary for the formation of high-quality films.
Abstract: : Long-chain alkanethiols, HS(CH2)nX, adsorb from solution onto gold surfaces and form ordered, oriented monolayer films. The properties of the interfaces between the films and liquids are largely independent of chain length when n > 10; in particular, wetting is not directly influenced by the proximity of the underlying gold substrate. The specific interaction of gold with sulfur and other soft nucleophiles and its low reactivity toward most hard acids and bases make it possible to vary the structure of the terminal group, X, widely and thus permit the introduction of a great range of functional groups into a surface. Studies of wettability of these monolayers, and of their composition using X-ray photoelectron spectroscopy (XPS), indicate that the monolayers are oriented with the tail group, X, exposed at the monolayer-air or monolayer- liquid interface. The adsorption of simple n-alkanethiols generates hydrophobic surfaces whose free energy (19 mJ/sq. m) is the lowest of any hydrocarbon surface studied to date. Measurement of contact angles is a useful tool for studying the structure and chemistry of the outermost few angstroms of a surface. This work used contact angles and optical ellipsometry to study the kinetics of adsorption of monolayer films and to examine the experimental conditions necessary for the formation of high-quality films.
3,193 citations
3,054 citations
3,009 citations
Book•
12 May 1991
TL;DR: In this paper, the authors present a model of self-assembled monolayers for the analysis of surface properties of Langmuir-Blodgett (LB) and Self-Assembled Monolayers (SA) films.
Abstract: Analytical Tools. Analysis of Film Properties. Analysis of Surface Properties. Langmuir-Blodgett Films. Self-Assembled Monolayers. Modeling of LB and SA Monolayers. Applications of LB and SA Films. Author's Final Note. Index.
2,775 citations