Anion recognition and redox sensing by a metalloporphyrin–ferrocene–alkylammonium conjugate

Bucher, Christophe; Devillers, Charles H.; Moutet, Jean‐Claude; Royal, Guy; Saint‐Aman, Eric

doi:10.1039/b411870g

Cited by 62 publications

(62 citation statements)

References 44 publications

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“…13 The overwhelming majority of reported metallocenyl-substituted porphyrins are composed of redox-active ferrocenyl moieties appended to the meso or to the b positions of the tetrapyrrolic macrocycle. Besides the well-known potentialities brought about by these substituents (redox-driven fluorescence switches 14 or sensors, 15 photo-induced electron transfer processes 16 for solar energy conversion 17 and molecular-based multibit information storage devices 18 ), additional exciting perspectives are expected if ferrocenyl groups are efficiently conjugated through the porphyrin core. Indeed, these compounds exhibit strong metal-metal coupling which is responsible for multiredox processes, magnetic coupling and unpaired electron density migration.…”

Section: Introductionmentioning

confidence: 99%

π-Interactions as a tool for an easy deposition of meso-tetraferrocenylporphyrin on surfaces

et al. 2013

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A bottom-up approach was employed to prepare novel Self-Assembled Monolayers (SAMs) in which a naphthyl moiety acted as a ''p-binder'' for unfunctionalised meso-tetraferrocenylporphyrin (H 2 TFcP).Four naphthalene derivatives with an appropriate functional group were synthesized and SAMs were prepared both on gold and ITO surfaces. Mixed H 2 TFcP-naphthalene films were thoroughly characterized using UV-Vis, XPS and electrochemical techniques. In particular, angle-dependent XPS experiments revealed an almost perpendicular orientation of the porphyrin on surfaces, suggesting that an intercalation occurred among naphthalene units. A large amount of porphyrin was deposited on both the surfaces (in the order of 10 À10 mol Â cm À2), comparable to that afforded by more conventional covalent linkages. However, significant differences in homogeneity between SAMs on gold and ITO resulted in a diverse electrochemical behaviour. The electrochemical activity of the oxidised porphyrin was restored by prolonged exposure of the modified gold electrode (tens of seconds) to a negative potential, whereas no response was detected after the same treatment on ITO. This novel approach provides a general and versatile strategy to bind meso-substituted porphyrins on a pre-formed monolayer without the necessity for further functionalisations.

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Section: Introductionmentioning

confidence: 99%

π-Interactions as a tool for an easy deposition of meso-tetraferrocenylporphyrin on surfaces

et al. 2013

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“…Several studies were devoted to their reciprocal interactions through the covalent bonds or supramolecular contacts. 1 Many dyads or triads containing ferrocenes and porphyrins were synthesized in order to investigate the energy and/or electron transfer induced by light.…”

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confidence: 99%

Synthesis and characterization of eight new tetraphenylporphyrins bearing one or two ferrocenes on the β-pyrrole positions

2013

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One or two ferrocenes were linked to the b-pyrrole positions of the free base TPP or its zinc complex through an ethynyl or ethynylenephenylene group using a modification of the Sonogashira method. All the compounds were characterized using UV-vis, FAB-mass and NMR spectroscopy and cyclic voltammetry.Ferrocenes and porphyrins are among the most intriguing molecules due to their electrochemical and catalytic properties. Several studies were devoted to their reciprocal interactions through the covalent bonds or supramolecular contacts. 1Many dyads or triads containing ferrocenes and porphyrins were synthesized in order to investigate the energy and/or electron transfer induced by light.2 Furthermore, different p-conjugated organic bridges were proposed and investigated as connecting molecular wires between several chromophores. They include oligo-phenylenevinylene, 3 oligo-phenyleneethynylenes, 4 oligo-acetylenes, 5 oligo-thiophenes, 6 and oligophenylenes. 7 In all these cases the wire-like behavior -efficient or inefficient -depends on the combination of several factors including the degree of conjugation in the bridge, orbital matching, donor-bridge energy gap, etc. 8During our investigations on the electronic properties of dyads containing porphyrins and fullerenes, we reported on the properties of dyads containing such monomers linked by oligo-ethynylenephenylene bridges. 9 The presence of one or more triple bonds connecting porphyrins and ferrocenes can provide interesting and unusual properties to the dyads due to their reciprocal electronic interactions and the rigidity of the structure.

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“…12,13 This abnormal adsorbed state was attributed to the chemical structure of FcUTMA, which has an ammonium ion and ferrocene group positioned at either end of the molecule. The anion sensing ability of ACFcCSs was reported by Reynes et al, [14][15][16] who investigated inorganic anions and ATP in predominantly organic media.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Sensing of Anions and Heparin by an Alkyl-chain Ferrocene Cationic Surfactant

et al. 2011

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Anion recognition and redox sensing by a metalloporphyrin–ferrocene–alkylammonium conjugate

Cited by 62 publications

References 44 publications

π-Interactions as a tool for an easy deposition of meso-tetraferrocenylporphyrin on surfaces

π-Interactions as a tool for an easy deposition of meso-tetraferrocenylporphyrin on surfaces

Synthesis and characterization of eight new tetraphenylporphyrins bearing one or two ferrocenes on the β-pyrrole positions

Electrochemical Sensing of Anions and Heparin by an Alkyl-chain Ferrocene Cationic Surfactant

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