Electrochemically driven interfacial halogen bonding on self-assembled monolayers for anion detection

Hijazi, Hussein; Vacher, Antoine; Groni, Sihem; Lorcy, Dominique; Levillain, Eric; Fave, Claire; Schöllhorn, Bernd

doi:10.1039/c8cc08856j

Cited by 29 publications

(39 citation statements)

References 53 publications

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“…5,6 This has also been exploited in electrochemical anion sensors in solution, [7][8][9][10][11] and, very recently, at receptive interfaces. [12][13][14] The surface-immobilisation of (redox-active) receptors is relevant to the development of real-life relevant sensors, [15][16][17][18] enabling facile sensor reuse, and sensing both under flow and in (aqueous) solvent media in which many synthetic receptors are not natively soluble. 1,19 Our quantitative understanding of anion sensing at redox-active interfaces, does, however, remain underdeveloped.…”

Section: Introductionmentioning

confidence: 99%

Enhanced voltammetric anion sensing at halogen and hydrogen bonding ferrocenyl SAMs

Hein

Beer

et al. 2021

Chem. Sci.

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Section: Introductionmentioning

confidence: 99%

Enhanced voltammetric anion sensing at halogen and hydrogen bonding ferrocenyl SAMs

Hein

Beer

et al. 2021

Chem. Sci.

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“…1,19 Our quantitative understanding of anion sensing at redox-active interfaces, does, however, remain underdeveloped. 14,18,[20][21][22] Often an enhanced sensory performance (larger signal magnitude) is observed on confining redox-active receptors to interfaces, 19, 23 but the specific physico-chemical origins of this remain poorly understood. It has been suggested that an enhanced interfacial binding strength, brought about by receptor preorganisation and/or cooperative/chelate effects is the origin of the surface-enhancement effect.…”

Section: -14mentioning

confidence: 99%

“…15, 20, 34 Although this has been attributed to surface confined receptor preorganisation and/or cooperative/chelate binding, this does not fully explain the observations herein. 14,15,20 Receptor immobilisation within compact films will reduce any entropic penalty associated with anion binding, but other factors, including receptor and anion dehydration, are likely to be important. More importantly, the magnitude of the voltammetric response is determined by the BEF and not the absolute magnitude of the binding (to any one receptor oxidation state).…”

Section: Comparison Of Diffusive and Surface-confined Sensor Responsementioning

confidence: 99%

Enhanced Voltammetric Anion Sensing at Halogen and Hydrogen Bonding Ferrocenyl SAMs

Hein

Li²,

Beer³

et al. 2020

Preprint

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Halogen bonding mediated electrochemical anion sensing has very recently been established as a potent platform for the selective and sensitive detection of anions, although the principles that govern binding and subsequent signal transduction remain poorly understood. Herein we address this challenge by providing a comprehensive study of novel redox-active halogen bonding (XB) and hydrogen bonding (HB) ferrocene-isophthalamide-(iodo)triazole receptors in solution and at self-assembled monolayers (SAMs). Under diffusive conditions the sensory performance of the XB sensor was significantly superior. In molecular films the XB and HB binding motifs both display a notably enhanced, but similar, response to specific anions. Importantly, the enhanced response of these films is rationalised by a consideration of the (interfacial) dielectric microenvironment. These effects, and the resolved relationship between anion binding and signal transduction, underpin an improved fundamental understanding of anion sensing at redox-active interfaces which will benefit not just the development of more potent, real-life relevant sensors, but also new tools to study host-guest interactions at interfaces.

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“…These relatives of the HB are hardly exotic academic novelties, but have a wide range of applications, such as serving as synthons in self-assembling networks [117], biological catalysis [118], oxidative addition [119], self-assembled monolayers [120], SN2 reaction catalysis [121], design of functional mesomorphic materials [122], and even directed construction of supramolecular quadruple and double helices [123]. One of the more interesting uses concerns selective binding of anions [124][125][126][127][128][129][130][131].…”

Section: Cousins Of Hbsmentioning

confidence: 99%

Forty years of progress in the study of the hydrogen bond

Scheiner

2019

Struct Chem

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The author looks back at developments over the last few decades concerning the H-bond. The list of atoms involved as proton donor and acceptor has broadened dramatically, including most electronegative atoms and even metals. The factors that control the transfer of the proton across the H-bond have been elucidated and show the importance of even minor changes in its geometry. Small stretches can shut down the transfer entirely and certain bends can force a proton to transfer against a pK gradient. Along with recognition that a CHꞏꞏO interaction can represent a true H-bond, and one with strength comparable to more traditional H-bonds, has come an understanding of its contributions to protein structure and function. The replacement of the bridging H by any of a litany of electronegative atoms leads to similarly strong interactions, with many features virtually indistinguishable from a true H-bond. These noncovalent interactions are typically referred to as halogen, chalcogen, pnicogen, and tetrel bonds, depending upon the identity of the substitute bridging atom.

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Electrochemically driven interfacial halogen bonding on self-assembled monolayers for anion detection

Abstract: The concept of anion detection via reversible electrochemically driven charge-assisted halogen bonding in solution was transferred on the surface.

Cited by 29 publications

References 53 publications

Enhanced voltammetric anion sensing at halogen and hydrogen bonding ferrocenyl SAMs

Enhanced voltammetric anion sensing at halogen and hydrogen bonding ferrocenyl SAMs

Enhanced Voltammetric Anion Sensing at Halogen and Hydrogen Bonding Ferrocenyl SAMs

Forty years of progress in the study of the hydrogen bond

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