A Convenient Preparation of Monolithioferrocene<sup>1</sup>

Goldberg, Stanley I.; Keith, Lawrence H.; Prokopov, Theodore S.

doi:10.1021/jo01038a502

Cited by 29 publications

(16 citation statements)

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“…Ch1oroferrocene.-To a stirred solution of ferrocene (20.2 g, 0.109 mol) in dry ether (500 cm3) was added a LiBu"-hexane solution (220 cm3 of 0.49 mol dm-,, 0.108 mol) and stirred for 6 h. 57 The flask was then cooled to -78 "C and distilled tosyl (toluene-p-sulphonyl) chloride (23.1 g, 0.12 mol) was added, the solution being stirred a further 3 h at -78 "C, then left overnight. Water (3 cm3) was added, after which the solution was filtered through Celite and rapidly chromatographed (activity I1 alumina) with light petroleum (b.p.…”

Section: Methodsmentioning

confidence: 99%

Analysis of substituted ferrocenes by infrared spectroscopy

Phillips¹,

Lacey²,

Cooper³

1988

J. Chem. Soc., Dalton Trans.

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Section: Methodsmentioning

confidence: 99%

Analysis of substituted ferrocenes by infrared spectroscopy

Phillips¹,

Lacey²,

Cooper³

1988

J. Chem. Soc., Dalton Trans.

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“…First, was the reaction between the hydride-terminated silicon surface and the alkenyl halide (hydrosilylation reaction) activated by white light 20 . Following this, the modified surface was put in a monolithio-ferrocene solution, previously synthesized according to prior studies [30][31] . In order get different length alkyl-ferrocene chains, alkelyn halide of different number of carbon atoms were employed: 3-bromo 1propene; 5-bromo 1-pentene; and 10-bromo 1-decene.…”

Section: Surface Modificationmentioning

confidence: 99%

Electron Transfer Rates of Alkyl-Ferrocene Molecules Forming Incomplete Monolayer on Silicon Electrodes

Riveros

Meneses

Escobar

et al. 2010

J. Chil. Chem. Soc.

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This study shows the results obtained when binding alkyl ferrocene molecules on silicon surface forming incomplete monolayers. The electrodic surface functionalization is carried out by a two step procedure: First, a hydrosilytation reaction between a Si-H surface and an alkenyl bromide active by white light; and then, the reaction of this surface with a monolithio ferrocene solution. Alkenyl bromide with different numbers of carbon atoms (3, 5 and 10 carbon atoms) were employed in order to obtain propyl, pentyl and decyl ferrocene chains on the electrodic surface. The samples of modified silicon were analyzed by X-ray photoelectron spectroscopy (XPS) and electrochemical measurements confirming the presence of ferrocene molecules on the electrode surface. The results obtained show that in each and every case, there were incomplete monolayers on the silicon surface, ranging from 16% to 42 %, depending on the alkenyl bromide employed in the synthesis. AC voltammetry was employed to determine the kinetic of the electron transfer between ferrocene molecules and the silicon electrode. However, the rate constant is not influenced by the length of the alkyl chain, and is usually constant (2.01 s-1-3.66 s-1). The result above is due to the electron transfer process which is determine by electron hopping in a regime of bonded diffusion and not by a long-rate electron transfer such as in a full compact monolayer.

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“…The monolithio ferrocene was synthesized according to Goldberg et al 26 and Rebiere et al 27 It was used immediately in the same solution. The silicon samples modified with allyl bromide were put in contact with a solution of monolithio ferrocene during 1 h. The reaction between them is similar to that reported in the formation of alkyl ferrocenes reaction.…”

Section: Reaction With Monolithio Ferrocenementioning

confidence: 99%

Modification of silicon surface with redox molecules derived from ferrocene

Riveros¹,

González²,

Chornik³

2010

J. Braz. Chem. Soc.

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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...

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A Convenient Preparation of Monolithioferrocene¹

Cited by 29 publications

References 0 publications

Analysis of substituted ferrocenes by infrared spectroscopy

Analysis of substituted ferrocenes by infrared spectroscopy

Electron Transfer Rates of Alkyl-Ferrocene Molecules Forming Incomplete Monolayer on Silicon Electrodes

Modification of silicon surface with redox molecules derived from ferrocene

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A Convenient Preparation of Monolithioferrocene1

Cited by 29 publications

References 0 publications

Analysis of substituted ferrocenes by infrared spectroscopy

Analysis of substituted ferrocenes by infrared spectroscopy

Electron Transfer Rates of Alkyl-Ferrocene Molecules Forming Incomplete Monolayer on Silicon Electrodes

Modification of silicon surface with redox molecules derived from ferrocene

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A Convenient Preparation of Monolithioferrocene¹