Sterically Hindered Diazonium Salts for the Grafting of a Monolayer on Metals

Combellas, Catherine; Kanoufi, Frédéric; Pinson, Jean; Podvorica, Fetah I.

doi:10.1021/ja8018912

Cited by 228 publications

(184 citation statements)

References 21 publications

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“…113 As depicted in Fig. 6b, in order to prevent the growth of a polyaryl system, successful approaches include (i) sterically hindering the 3,5-positions, 114 and (ii) the use of very bulky protecting groups. 115 Fig .…”

Section: Aryl Diazonium Salt Derived Layersmentioning

confidence: 99%

The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies

2011

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The modification of surfaces with self-assembled monolayers (SAMs) containing multiple different molecules, or containing molecules with multiple different functional components, or both, has become increasingly popular over the last two decades. This explosion of interest is primarily related to the ability to control the modification of interfaces with something approaching molecular level control and to the ability to characterise the molecular constructs by which the surface is modified. Over this time the level of sophistication of molecular constructs, and the level of knowledge related to how to fabricate molecular constructs on surfaces have advanced enormously. This critical review aims to guide researchers interested in modifying surfaces with a high degree of control to the use of organic layers. Highlighted are some of the issues to consider when working with SAMs, as well as some of the lessons learnt (169 references). 2011 The Royal Society of Chemistry. The modification of surfaces with self-assembled monolayers (SAMs) containing multiple different molecules, or containing molecules with multiple different functional components, or both, has become increasingly popular over the last two decades. This explosion of interest is primarily related to the ability to control the modification of interfaces with something approaching molecular level control and to the ability to characterise the molecular constructs by which the surface is modified. Over this time the level of sophistication of molecular constructs, and the level of knowledge related to how to fabricate molecular constructs on surfaces have advanced enormously. This critical review aims to guide researchers interested in modifying surfaces with a high degree of control to the use of organic layers. Highlighted are some of the issues to consider when working with SAMs, as well as some of the lessons learnt (169 references).

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Section: Aryl Diazonium Salt Derived Layersmentioning

confidence: 99%

The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies

2011

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“…Introduction of sterically encumbered substituents on the aryl rings has been successfully used to prevent the uncontrolled polymerization process, thus allowing the formation of a near monolayer 27 . However, an undesirable counterback is the chemical inertness of these molecules, which precludes further functionalization.…”

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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

122

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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“…The thickness of these multilayers can be optimized by changing the electrografting parameters, such as the applied potential, the grafting time or the diazonium concentration. 26,38) Various techniques have been described to prevent multilayer formation, including the use of diazonium salts with sterically hindering groups 39) or sacrificial protection groups, 33) or via electrografting of calixarene molecules. 35) Figure 4 shows the fluorescence results following a synthesis run with a Cy3-labeled phosphoramidite (5A-Cy3-3A).…”

Section: Electrode Functionalization and Characterizationmentioning

confidence: 99%

Direct on-chip DNA synthesis using electrochemically modified gold electrodes as solid support

Levrie

Jans

Schepers

et al. 2018

Jpn. J. Appl. Phys.

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DNA microarrays have propelled important advancements in the field of genomic research by enabling the monitoring of thousands of genes in parallel. The throughput can be increased even further by scaling down the microarray feature size. In this respect, microelectronics-based DNA arrays are promising as they can leverage semiconductor processing techniques with lithographic resolutions. We propose a method that enables the use of metal electrodes for de novo DNA synthesis without the need for an insulating support. By electrochemically functionalizing gold electrodes, these electrodes can act as solid support for phosphoramidite-based synthesis. The proposed method relies on the electrochemical reduction of diazonium salts, enabling site-specific incorporation of hydroxyl groups onto the metal electrodes. An automated DNA synthesizer was used to couple phosphoramidite moieties directly onto the OH-modified electrodes to obtain the desired oligonucleotide sequence. Characterization was done via cyclic voltammetry and fluorescence microscopy. Our results present a valuable proof-of-concept for the integration of solid-phase DNA synthesis with microelectronics.

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Sterically Hindered Diazonium Salts for the Grafting of a Monolayer on Metals

Cited by 228 publications

References 21 publications

The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies

The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies

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

Direct on-chip DNA synthesis using electrochemically modified gold electrodes as solid support

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