Conducting Ferrocene Monolayers on Nonconducting Surfaces

Hauquier, Fanny; Ghilane, Jalal; Fabre, Bruno; Hapiot, Philippe

doi:10.1021/ja711147f

Cited by 92 publications

(96 citation statements)

References 12 publications

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“…Chemically modified surfaces were already the subject of many studies in the last decades since they find application in numerous areas including electrocatalysis, [114] [115] corrosion protection, [116] molecular electronics, [117] [118] integrated circuits, [119] [120] information storage, [120]- [122] sensing [123] [124] and many others.…”

Section: Surface Modificationmentioning

confidence: 99%

“…[119] More recently, some new techniques were proposed to enhance and diversify the number of method that can be used to chemically modify surfaces. For example, the introduction of functional groups via Grignard reaction on chlorinated or brominated carbon surfaces, [144] or via photochemical functionalization of acyl chloride modified surfaces.…”

Section: The Sonogashira Reactionmentioning

confidence: 99%

“…[226]- [229] It has been successfully applied in numerous areas ranging from corrosion protection of bulk surfaces [116] to the integration of selective functionalities in nano sensing devices. [119][122] [120] For electronic applications the modification of conducting surfaces at the molecular level with functional active building blocks represents a promising approach to new electrodes with tailor made surface chemistry. [128] Strategies based on the stepwise functionalization of surfaces have already been reported.…”

Section: Platinum Electrode Modificationmentioning

confidence: 99%

“…[143] Often, the first step is the introduction of a functional group via a suitable organic molecule as self assembled monolayer (SAM) on a noble metal substrate, [230][231] silicon or silicon oxide surfaces [125] [127] or as coating ligand for nanoparicles. [152] After the introduction of a chemically addressable surface layer, efficient chemical conditions such as click chemistry [142][228] [232] or peptide coupling [119] have been applied to further diversify the exposed surface functionality.…”

Section: Platinum Electrode Modificationmentioning

confidence: 99%

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Shape‐Switchable Azo‐Macrocycles

et al. 2009

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The synthesis of four shape‐switchable macrocycles comprising different peripheral substituents is described. The macrocycles 1–4 consist of m‐terphenyl semicircles interlinked by two azo joints. These macrocycles were assembled from nitro‐functionalized m‐terphenyl moieties through reductive dimerization. The semicircles were assembled through Suzuki cross‐coupling reactions. The molecular weights of the macrocycles were determined by vapour pressure osmometry, because mass spectrometry failed in the cases of 2 and 3. The E → Z photoisomerization reactions were analysed by UV/Vis spectroscopy complemented by 1H NMR studies. A very slow thermal back‐reaction indicated considerable stabilization of the Z isomer. The reduced efficiency of the thermal back‐reaction probably arises from the reduced degree of freedom due to the mechanical interlinking of the two azo groups. The photostationary state consisted of all‐Z (85 %) and all‐E isomers (15 %). The E → Z transformation induced by irradiation displayed simple exponential kinetics, which indicates pairwise switching of the two azo groups in a macrocycle, at least on the timescale under investigation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Surface Modificationmentioning

confidence: 99%

Section: The Sonogashira Reactionmentioning

confidence: 99%

Section: Platinum Electrode Modificationmentioning

confidence: 99%

Section: Platinum Electrode Modificationmentioning

confidence: 99%

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Shape‐Switchable Azo‐Macrocycles

et al. 2009

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“…Indeed, the surface coverages reached for high-quality ferrocenyl monolayers are in the range of (2.0-5.0) 10 À10 mol cm À2 . This does not only allow for an extremely fast electron communication between the electroactive groups, [5] but also yields charge densities in the range of 20-50 mC cm À2 …”

mentioning

confidence: 99%

Light‐Activated Electroactive Molecule‐Based Memory Microcells Confined on a Silicon Surface

Fabre

Scheres

et al. 2013

Angewandte Chemie

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Among the existing charge-storage devices of modern computers, the dynamic random access memory (DRAM) provides the most interesting opportunity of integrating redoxactive molecular components.[1] The capacitance density of todays DRAM storage cell is on the order of 50-100 fF mm À2(5-10 mF cm À2 ) with a benchmark cell size below the squaremicrometer range. In this context, ferrocene (Fc) and metalcomplexed porphyrins have been explored as the most promising memory elements, because they show, both in solution and confined on surfaces, one to several perfectly reversible and stable one-electron redox reactions within an attractive potential window, that is, 0.0 to 1.0 V vs. a saturated calomel electrode (SCE). Therefore, the functionalization of technologically relevant conducting surfaces, such as oxidefree, hydrogen-terminated silicon (H-Si), with high-quality Fc-terminated [2][3][4][5][6][7][8] and metal-complexed porphyrin-terminated [9][10][11][12] monolayers has been demonstrated to be a powerful bottom-up approach for the fabrication of electrically addressable charge-storage devices with low-power consumption. Compared with metalloporphyrins, Fc is a much smaller molecule (average diameter of tetraphenylporphyrin and Fc are about 18 and 6.6 , respectively), and consequently is immobilized on silicon with a higher surface coverage, which gives rise to higher charge densities. Indeed, the surface coverages reached for high-quality ferrocenyl monolayers are in the range of (2.0-5.0) 10 À10 mol cm À2 . This does not only allow for an extremely fast electron communication between the electroactive groups, [5] but also yields charge densities in the range of 20-50 mC cm À2

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Modular Functionalization of Electrodes by Cross‐Coupling Reactions at Their Surfaces

Müri

Gotsmann

Leroux

et al. 2011

Adv Funct Materials

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International audienceDue to the increasing importance of modified electrodes for many applications in nanotechnology, including molecular electronics, bioelectronics, and sensors, there is a need to find ways to chemically attach suitable molecular films onto the electrodes. Combining the electroreduction of aryl diazonium salts with the Sonogashira cross-coupling reaction, a new modular technique to modify electrodes is presented. The new technique allows a wide range of functional groups to be introduced onto electrode surfaces with high surface coverage by the functional subunit. Various organic subunits, including redox chromophores, are successfully attached to platinum electrodes. The corresponding films are characterized using cyclic voltammetry, X-ray photoelectron spectroscopy, atomic force microscopy, and contact-angle measurements. The electroreduction of diazonium salts is successfully achieved on a broad variety of conducting and semiconducting surfaces, which shows that the technique is applicable to a broad variety of substrates

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Conducting Ferrocene Monolayers on Nonconducting Surfaces

Cited by 92 publications

References 12 publications

Shape‐Switchable Azo‐Macrocycles

Shape‐Switchable Azo‐Macrocycles

Light‐Activated Electroactive Molecule‐Based Memory Microcells Confined on a Silicon Surface

Modular Functionalization of Electrodes by Cross‐Coupling Reactions at Their Surfaces

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