Self-assembled monolayers of alkanethiols on gold: comparisons of monolayers containing mixtures of short- and long-chain constituents with methyl and hydroxymethyl terminal groups

Folkers, John P.; Laibinis, Paul E.; Whitesides, George M.

doi:10.1021/la00041a015

Cited by 383 publications

(425 citation statements)

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“…1b) 12 . Dilution strategies with unfunctionalized alkylthiols allowing strong packing of the alkyl chain at the surface and simultaneous connection of large functional objects at the surface often lead to small 'islands of objects' , not to regular distribution at the surface 12,[15][16][17][18][19] . An alternative strategy for connecting organic moieties onto electrodes is the reductive grafting of aryldiazonium salts that yields covalent attachment of phenyl derivatives onto the surface.…”

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confidence: 99%

Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization

Mattiuzzi¹,

Jabin²,

Mangeney³

et al. 2012

Nat Commun

120

174

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An essential issue in the development of materials presenting an accurately functionalized surface is to achieve control of layer structuring. Whereas the very popular method based on the spontaneous adsorption of alkanethiols on metal faces stability problems, the reductive electrografting of aryldiazonium salts yielding stable interface, struggles with the control of the formation and organization of monolayers. Here we report a general strategy for patterning surfaces using aryldiazonium surface chemistry. Calix[4]tetra-diazonium cations generated in situ from the corresponding tetra-anilines were electrografted on gold and carbon substrates. The well-preorganized macrocyclic structure of the calix[4]arene molecules allows the formation of densely packed monolayers. Through adequate decoration of the small rim of the calixarenes, functional molecules can then be introduced on the immobilized calixarene subunits, paving the way for an accurate spatial control of the chemical composition of a surface at molecular level.

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mentioning

confidence: 99%

Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization

Mattiuzzi¹,

Jabin²,

Mangeney³

et al. 2012

Nat Commun

120

174

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“…21,22 The distribution of each component in a mixed SAM is determined by the type of functional group (linker and/or tail group), chain length and the fabrication process. 23,24 The study of combinations of short and long alkyl chain functionalization suggested the stability order to be long-long > short-short > long-short 6 which clearly demonstrates the key role of mixed functionalization in determining the stability of the SAMs on metals. In one interesting application Frederix et al 25 studied a biosensor interface consisting of mixed SAMs of thiols with carboxylic and hydroxyl or poly (ethylene glycol) on gold.…”

Section: Introductionmentioning

confidence: 92%

Binary functionalization of H:Si(111) surfaces by alkyl monolayers with different linker atoms enhances monolayer stability and packing

Arefi

Nolan

Fagas

2016

Phys. Chem. Chem. Phys.

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Original citationArefi, H. H., Nolan, M. and Fagas, G. (2016) Previous studies have shown that the linker atom, through which the monolayer binds to the Si substrate, and any tail group in the alkyl chain, can tune the monolayer stability and electronic properties. In this paper we study the H:Si(111) surface functionalized with binary SAMs: these are composed of alkyl chains that are linked to the surface by two different linker groups. Aiming to enhance SAM stability and increase coverage over singly functionalized Si, we examine with density functional theory simulations that incorporate vdW interactions, a range of linker groups which we denote as -X-(alkyl) with X = CH2, 2 O(H), S(H) or NH(2) (alkyl = C6 and C12 chains). We show how the stability of the SAM can be enhanced by adsorbing alkyl chains with two different linkers, e.g. Si-[C,NH]-alkyl, through which the adsorption energy is increased compared to functionalization with the individual -X-alkyl chains. Our results show that it is possible to improve stability and optimum coverage of alkyl functionalized SAMs linked through a direct Si-C bond by incorporating alkyl chains linked to Si through a different linker group, while preserving the interface electronic structure that determines key electronic properties. This is important since any enhancement in stability and coverage to give more densely packed monolayers will result in fewer defects. We also show that the work function can be tuned within the interval of 3.65 -4.94 eV (4.55 eV for bare H:Si (111)).

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“…Surface compositions of mixed SAMs were measured by X-ray photoelectron spectroscopy (XPS; AXIS-HS, Kratos, Manchester, UK) 29,30) . This measurement was performed under 10 -7 Pa. Al-Kα monochromatic X-ray was irradiated under the condition of 15 kV accelerated voltage and 10 mA filament electric current.…”

Section: Characterization Of Mixed Sam Surfacesmentioning

confidence: 99%

Cell Adhesion and Proliferation Patterns on Mixed Self-assembled Monolayers Carrying Various Patios of Hydroxyl and Methyl Groups

et al. 2007

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Mixed self-assembled monolayers (SAMs) with hydroxyl and methyl surface groups were prepared as biomaterial surface models which were well-controlled and well-defined. The surface properties of mixed SAMs were examined by X-ray photoelectron spectroscopy and water contact angle measurement. It was found that the parameter of water contact angle more accurately reflected the surface compositions of mixed SAMs than by the mixing ratio of the two alkanethiols. Cell adhesion and growth were also examined on mixed SAMs of various wettability conditions. It was found that amount of serum protein adsorption changed with the surface composition. To examine the effect of surface composition on cell growth pattern, four cell types -C3H10T1/2-clone 8, L929, UVB6-2.1A, and MC3T3E1 -were incubated on mixed SAMs for three or six days. Differences in cell growth pattern against wettability were clearly recognized for each cell type. In light of the results obtained in this study, the relationship between the biocompatibility of biomaterials and surface factors were thus clarified.

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Self-assembled monolayers of alkanethiols on gold: comparisons of monolayers containing mixtures of short- and long-chain constituents with methyl and hydroxymethyl terminal groups

Cited by 383 publications

References 0 publications

Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization

Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization

Binary functionalization of H:Si(111) surfaces by alkyl monolayers with different linker atoms enhances monolayer stability and packing

Cell Adhesion and Proliferation Patterns on Mixed Self-assembled Monolayers Carrying Various Patios of Hydroxyl and Methyl Groups

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