Self-assembled monolayers of a tetrathiafulvalene-based redox-switchable ligand

Trippé, Gaëlle; Oçafrain, Maïténa; Besbes, Mohamed; Monroche, Vincent; Lyskawa, Joël; Derf, Franck Le; Sallé, Marc; Becher, Jan; Colonna, Barbara; Echegoyen, Luís

doi:10.1039/b204996a

Cited by 31 publications

(18 citation statements)

References 29 publications

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“…[1b,c] Depending on the nature of the functional units, such SAMs can be utilised for diverse applications. For example, redoxactive adsorbate species based on tetrathiafulvalene, [3] ferrocene and porphyrin [4] have been widely used for electrode modification and related purposes. [5] We have focused our attention on 1,1'-disubstituted ferrocene derivatives which contain two identical anchor groups suitable for chemisorption on gold and have already described results concerning SAM formation with 1,1'-diisocyanoferrocene (1), 1,1'-diisothiocyanatoferrocene (2) and 1,1'-bis(diphenylphosphanyl)-ferrocene (dppf, 3) investigated in situ and in real time by second harmonic generation (SHG).…”

Section: Introductionmentioning

confidence: 99%

Dipodal Ferrocene‐Based Adsorbate Molecules for Self‐Assembled Monolayers on Gold

Weidner

Ballav

Zharnikov

et al. 2008

Chemistry A European J

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1,1'-Difunctionalised ferrocene derivatives have been studied, which contain groups suitable for chemisorption on gold substrates, namely -NC, -PR(2) as well as a range of sulfur-containing units like -NCS, -SR, and thienyl. Thin films on gold have been fabricated from solution with most of these adsorbate species. Film thickness, composition and structure were investigated primarily by X-ray photoelectron and near-edge X-ray absorption fine-structure spectroscopy. The quality of self-assembled monolayers fabricated from 1,1'-diisocyanoferrocene (1) and 1,1'-diisothiocyanatoferrocene (2) turned out to be superior to that of films based on the other adsorbate species investigated. In addition to the surface coordination behaviour of 1 towards gold substrates, relevant aspects of the molecular coordination chemistry of 1 have also been addressed, including the synthesis and characterisation of [(mu-1){Cr(CO)(5)}(2)], [Ag(2)(mu-1)(2)](NO(3))(2) x H(2)O and [(mu-1)(AuCl)(2)]. The crystal structure of the gold complex is governed by aurophilic interactions and can be taken as a model for the arrangement of 1 in self-assembled monolayers on gold.

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Section: Introductionmentioning

confidence: 99%

Dipodal Ferrocene‐Based Adsorbate Molecules for Self‐Assembled Monolayers on Gold

Weidner

Ballav

Zharnikov

et al. 2008

Chemistry A European J

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“…17 A slightly different approach is evident in preparation of the methylthio-TTFs 16 bearing thiol-terminated C 3 and C 6 chains (Scheme 5). 20 In this case a step is saved by reacting the cyanoethyl compound 14 with base then a bromide already containing the acetylthio group to give 15. Diisobutylaluminium hydride is then used reduce off the acetyl group to generate the thiol 16.…”

Section: Ttfs With a Single Longer Chain Thiol Tethermentioning

confidence: 99%

“…Diisobutylaluminium hydride is then used reduce off the acetyl group to generate the thiol 16. Exactly the same approach was also applied to synthesis of the crown ether analogues 17, which were studied as potential electrochemical sensors for Ba 2+ at a gold electrode, 20 and similar metal-chelating acyclic polyether analogues. 21 Crown ether-containing TTF derivatives have been of considerable interest for ion sensor applications and several other derivatives suitable for adsorption on gold have been prepared (Scheme 6).…”

Section: Ttfs With a Single Longer Chain Thiol Tethermentioning

confidence: 99%

Synthesis of Electro-active Compounds Suitable for Adsorption on Metal Surfaces

Aitken

Jethwa

2017

Organic Preparations and Procedures International

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“…Electrode surface modification with TTF derivatives has already been described by formation of self‐assembly monolayers (SAMs) from mercapto or disulfide TTF derivatives,7 or by electropolymerization of TTF functionalized thiophene‐based precursors 8. In the course of our studies on related aspects dedicated to electrode surface modifications with TTF moieties, we have developed the preparation of crown‐TTF SAMs,9 and we have also carried out an original film electrodeposition of TTF‐based dendrimers 10. Furthermore, we have preliminary demonstrated the high efficiency of a post‐polymerization surface functionalization process…”

Section: Introductionmentioning

confidence: 99%

Crown‐Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties

Trippé

Derf

Lyskawa

et al. 2004

Chemistry A European J

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A crown-tetrathiafulvalene electroactive receptor has been covalently linked to electropolymerizable pyrrole or 3,4-ethylenedioxythiophene monomers. The synthetic route to the monofonctionalized tetrathiafulvalene (TTF) ligand has been optimized. Two derivatives of pyrrole (N- and 3-substituted) were synthesized. The various substituted monomers have been electropolymerized to produce polypyrrole (PP) and poly(ethylenedioxothiophene) (PEDOT) films bearing the electroactive TTF moiety. The electroactivity of the polymer films is efficiently controlled by the well-defined two-step redox behavior of the TTF unit. In the case of PEDOT, an alternative post-polymerization derivatization strategy has been used, involving the grafting of the crown-TTF ligand on the previously grown PEDOT backbone. Though chemical derivatization is realized under heterogeneous conditions, in the bulk of the film, this strategy proved to be particularly efficient. These electrodes constitute the first examples of conducting polymer-based modified electrodes incorporating a TTF electrochemical probe, able to interact with a guest ion, such as Ba2+. The cation recognition properties of these various electrodes have been analyzed by cyclic voltammetry and their electroactivity in water as well as their regeneration capability have been investigated.

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Self-assembled monolayers of a tetrathiafulvalene-based redox-switchable ligand

Cited by 31 publications

References 29 publications

Dipodal Ferrocene‐Based Adsorbate Molecules for Self‐Assembled Monolayers on Gold

Dipodal Ferrocene‐Based Adsorbate Molecules for Self‐Assembled Monolayers on Gold

Synthesis of Electro-active Compounds Suitable for Adsorption on Metal Surfaces

Crown‐Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties

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