A mild functionalization route to robust molecular electroactive monolayers on Si(100)

Zanoni, R.; Aurora, Annalisa; Cattaruzza, Fabrizio; Coluzza, C.; Dalchiele, Enrique A.; Decker, F.; Santo, Giovanni Di; Flamini, Alberto; Funari, L.; Marrani, Andrea Giacomo

doi:10.1016/j.msec.2005.09.086

Cited by 24 publications

(30 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…15 Numerous studies have been carried out to understand the interfacial processes during the electron transfer in redox self-assembled monolayers. 29 Vol.…”

Section: Electrochemical Characterizationmentioning

confidence: 99%

“…The general mechanism of these reactions involves the double bond addition to the Si-H surface, 9 where double bond homolytic cleavage is achieved by reaction with peroxides, 10 by UV irradiation, 11 by thermal activation, 12 by electrochemical processes, 13,14 or more recently, by white light irradiation. [15][16][17][18] The union of electroactive molecules on the silicon surface opens a new route for the making of hybrid devices, in which the properties of current silicon technology are combined with those of the molecules own. In the case of silicon, these hybrid components are ideal for Modification of Silicon Surface with Redox Molecules Derived from Ferrocene J. Braz.…”

mentioning

confidence: 99%

“…Commercially available ferrocene precursors as those used by Decker and co-workers, [15][16][17] and Li and co-workers [19][20][21] are scarce, limiting the number of the studied systems. A different route is followed by Fabre and Hauquier 22 who attach an amine-substituted ferrocene derivative to a pre-assembled acid-terminated alkyl monolayer through several chemical steps.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Modification of silicon surface with redox molecules derived from ferrocene

Riveros¹,

González²,

Chornik³

2010

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Este estudo apresenta um método novo para ligar moléculas redox ativas derivadas de ferroceno à superfície de silicone monocristalino. O procedimento consiste na reação de silicone hidrogenado com brometo de alila ativado com luz branca e sua reação subseqüente com monolítio ferroceno para criar uma união covalente entre a molécula redox e a superficie do semicondutor. As camadas formadas são eletroquimicamente ativas e apresentam um processo electroquímico quasi-reversível, atribuído às moléculas de ferroceno ligadas à superfície de silicone. A análise por espectroscopia fotoeletrônica de raios-X (XPS) confirma a presença de moléculas de ferroceno na superficie de silicone.This study presents a new method to bind active redox molecules derived of ferrocene to the surface of single crystal silicon. The procedure consists in the reaction of hydrogenated silicon with allyl bromide activated with white light and its subsequent reaction with monolithio ferrocene in order to create a covalent union between the redox molecule and the semiconductor surface. The layers formed are electrochemically active and present a quasireversible electrochemical process which is attributed to the ferrocene molecules which are bound to the silicon surface. X-ray photoelectron spectroscopy (XPS) analysis confirms the presence of ferrocene molecules on the silicon surface.Keyword: silicon, ferrocene, surface modification, characterization IntroductionAlthough molecular electronics appears as a new alternative in the development of nanometric electronic devices, 1 the production of transistors and other electronic devices is still dominated by silicon technology. Contributions to the transition between both technologies centered in the development of hybrid semiconductormolecule materials are therefore of paramount importance. 2In this field, there are several studies referring to the preparation and redox property studies of self-assembled monolayers (SAMs) on silicon surfaces. The formation of SAMs on oxidized silicon surfaces has been well documented.3-5 However, the Si-O bond is in general unfavorable for electronic applications because of a generally poor molecule-electrode electron transfer. Much better results are obtained in absence of the oxide layer through a direct Si-C union linkage. 6The formation of the Si-C bond has been usually performed by ultra high vacuum (UHV) techniques, 7-9 or by radicalary processes.3,9 The latter have been studied more thoroughly due to the relatively low operation cost. The general mechanism of these reactions involves the double bond addition to the Si-H surface, 9 where double bond homolytic cleavage is achieved by reaction with peroxides, 10 by UV irradiation, 11 by thermal activation, 12 by electrochemical processes, 13,14 or more recently, by white light irradiation. [15][16][17][18] The union of electroactive molecules on the silicon surface opens a new route for the making of hybrid devices, in which the properties of current silicon technology are combined with those of the molecules own...

show abstract

“…15 Numerous studies have been carried out to understand the interfacial processes during the electron transfer in redox self-assembled monolayers. 29 Vol.…”

Section: Electrochemical Characterizationmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Modification of silicon surface with redox molecules derived from ferrocene

Riveros¹,

González²,

Chornik³

2010

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…The presence of Fe III -related species indicates there was a sizable oxidation of the ferrocene units to ferricenium species under the reaction conditions used. 48 As shown ) upon the oxidative coupling of alkyne 2. Further, as shown in Fig.…”

Section: Oxidative Acetylenic Heterocoupling At Modified Si(100) Surfmentioning

confidence: 92%

Oxidative acetylenic coupling reactions as a surface chemistry tool

Ciampi

James

Darwish

et al. 2011

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

A novel method to prepare redox monolayers on silicon electrodes has been developed that employs CuIcatalyzed oxidative acetylenic coupling reactions for molecular electronic type applications. As the first case study, ethynylferrocene was covalently immobilized onto an acetylene-terminated monolayer on a Si(100) surface to give a 1,3-diyne (CC-CC-) linked redox assembly. The derivatization process requires no protection/de-protection steps, nor activation procedures. The effect of the conjugated diyne linkage on the rate of electron transfer between tethered ferrocenyl units and the silicon electrode is benchmarked against well-established "click" products (i.e. 1,2,3-triazole linkage). The surfaces, after each step, are characterized thoroughly using X-ray reflectivity (XRR), X-ray photoelectron spectroscopy (XPS), electrochemical impedance spectroscopy (EIS) and cyclic voltammetry (CV). The coupling chemistry provides a useful strategy for functionalizing silicon surfaces and contributes to an expanding repertoire of wet chemistry routes for the functionalization of solid substrates. This journal is the Owner Societies. A novel method to prepare redox monolayers on silicon electrodes has been developed that employs Cu I -catalyzed oxidative acetylenic coupling reactions for molecular electronic type applications. As the first case study, ethynylferrocene was covalently immobilized onto an acetylene-terminated monolayer on a Si(100) surface to give a 1,3-diyne (CRC-CRC-) linked redox assembly. The derivatization process requires no protection/de-protection steps, nor activation procedures. The effect of the conjugated diyne linkage on the rate of electron transfer between tethered ferrocenyl units and the silicon electrode is benchmarked against well-established ''click'' products (i.e. 1,2,3-triazole linkage). The surfaces, after each step, are characterized thoroughly using X-ray reflectivity (XRR), X-ray photoelectron spectroscopy (XPS), electrochemical impedance spectroscopy (EIS) and cyclic voltammetry (CV). The coupling chemistry provides a useful strategy for functionalizing silicon surfaces and contributes to an expanding repertoire of wet chemistry routes for the functionalization of solid substrates.

show abstract

“…To date most of the research effort has been toward the preparation of either ferrocene-or phorphyrin-based redox architectures [7][8][9][10][11][12][13]. While on the one hand modular (i.e.…”

Section: Introductionmentioning

confidence: 99%

Silicon (100) surfaces modified by osmium bipyridine complexes

Ciampi

Lai

Gooding

2010

2010 International Conference on Nanoscience and Nanotechnology

View full text Add to dashboard Cite

Tethered osmium bypiridine-pyridine complexes [Os(bpy)2Clpy-R] were prepared from chemically modified non-oxidized silicon (100) electrodes. Pyridinyl groups at the distal end of self-assembled monolayers (SAMs)-modified silicon surfaces were used to coordinatively bind a representative osmium bipyridil complex precursor [Os(bpy)2Cl2]. SAMs presenting the putative osmium ligand were prepared by a step-wise procedure using click reactions of acetylene-terminated alkyl monolayers and isonicotinic acid azide derivatives. The redox properties of the modified Si(100) electrodes were characterized using cyclic voltammetry. 2010 IEEE. . SAMs presenting the putative osmium ligand were prepared by a stepwise procedure using 'click' reactions of acetylene-terminated alkyl monolayers and isonicotinic acid azide derivatives. The redox properties of the modified Si(100) electrodes were characterized using cyclic voltammetry.

show abstract

A mild functionalization route to robust molecular electroactive monolayers on Si(100)

Cited by 24 publications

References 50 publications

Modification of silicon surface with redox molecules derived from ferrocene

Modification of silicon surface with redox molecules derived from ferrocene

Oxidative acetylenic coupling reactions as a surface chemistry tool

Silicon (100) surfaces modified by osmium bipyridine complexes

Contact Info

Product

Resources

About