Ferrocenyl-triazolyl-tetrathiafulvalene assemblies: synthesis and electrochemical recognition properties

Zhao, Bang‐Tun; Liu, Lianwei; Li, Xiaochuan; Qu, Gui‐Rong; Belhadj, Esmah; Derf, Franck Le; Sallé, Marc

doi:10.1016/j.tetlet.2012.10.107

Cited by 11 publications

(7 citation statements)

References 24 publications

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“…Compounds 1a , 1b , 2a , 2b , 3a , 3b , 4a , and 25,27-dimethoxy-26,28-dihydroxy- p - tert -butylthiacalix[4]arene were synthesized according to the corresponding literature. All reactions were carried out under dry argon atmosphere.…”

Section: Methodsmentioning

confidence: 99%

Metal-Promoted Intermolecular Electron Transfer in Tetrathiafulvalene–Thiacalix[4]arene Conjugates and Tetrachlorobenzoquinone

et al. 2014

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In this work, two series of tetrathiafulvalene (TTF) and thiacalix[4]arene (TCA) conjugates (TTF-TCA) were designed by CuAAC click reactions. The results obtained from NMR and (1)H NMR NOE indicated that their conformations of thiacalix[4]arene framework may prefer to 1,3-alternate. The cyclic voltammograms of four TTF-TCA compounds containing electroactive TTF units were provided. Meanwhile, their intermolecular electron-transfer (ET) behaviors with tetrachlorobenzoquinone (Q) mediated by different metal ions, Sc(3+), Pb(2+), Ag(+), Cd(2+), and Zn(2+), in CH3CN-CH2Cl2 (V/V = 1:1) solution were studied and analyzed via UV-vis spectroscopy. It was determined that intermolecular ET between each TTF-TCA and Q ensemble was not observed without introduction of the metal ions mentioned above. The added specified metal ions most likely induced the intermolecular ET between TTF-TCA and Q ensemble, and the effects of Sc(3+) functions were the most imperative. The intermolecular ET also proved to be reliant on the structure of TTF-TCA, where TTF-TCA 7a and 7b were more effective than TTF-TCA 6a and 6b. The difference may be credited to TTF-TCA 7a or 7b possessing two independent TTF pendants and providing a more synergic coordination among the TTF radical cation and Q radical anion with a metal ion.

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Section: Methodsmentioning

confidence: 99%

Metal-Promoted Intermolecular Electron Transfer in Tetrathiafulvalene–Thiacalix[4]arene Conjugates and Tetrachlorobenzoquinone

et al. 2014

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“…The solvents were purified and dried by standard methods. Dithiafulvene 4a 4,4.42 mmol) and 4formylphenyl benzoate (1g, 4.42 mmol) were added under inert atmosphere to 5 mL of P(OEt) 3 . The reaction mixture was heated to 100 °C for 5h and then allowed to reach room temperature.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…2 Actually, a cyclic binding site is not an essential condition for the elaboration of electroactive receptors as it was shown that TTFs bearing acyclic attachment sites show also good selectivity for metal ions 3 and could be used in TTF assembly for this purpose. 4 In this field of host−guest chemistry, we have previously examined a series of crown ether substituted vinylogous tetrathiafulvalenes (TTFV) 1 as potential ligands toward various cations (see scheme 1). 5 The electrochemical detection of their binding ability is based on the modification brought by the complexation of the molecular motions triggered by the electron transfer.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Thanks to the redox active TTF core, the binding occurrence is detected by modifications of the redox behavior of the TTF ligand . Actually, a cyclic binding site is not an essential condition for the elaboration of electroactive receptors as it was shown that TTFs bearing acyclic attachment sites show also good selectivity for metal ions and could be used in TTF assembly for this purpose . In this field of host–guest chemistry, we have previously examined a series of crown ether substituted vinylogous tetrathiafulvalenes (TTFV) 1 as potential ligands toward various cations (see scheme ) .…”

Section: Introductionmentioning

confidence: 99%

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Vinylogous Tetrathiafulvalene Based Podands: Complexation Interferences on the Molecular Movements Triggered by Electron Transfer

et al. 2013

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Substituted vinylogous tetrathiafulvalenes (TTFVs) containing two freely moving polyoxyethyl chains were prepared. Investigations of their redox behaviors in organic solvent show that these TTFV could efficiently complex metallic dications such as Pb(2+) or Ba(2+), leading to considerable modifications of their electrochemical response. As main feature, the molecule senses the association between the TTFV core and the metallic dication through a modification of the molecular motion triggered by the electron transfer. The complexation creates a link between the two parts of the TTFV core, causing considerable changes in the nature of the molecular motion. The resulting behavior is totally unusual as the 2-positively charged TTFV(2+) appears to present the highest association constants with the metallic dication.

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“…In the other few published examples of TTF-triazole systems, with linkers of various lengths between TTF and triazole, 8 the latter serves mainly to connect other electroactive moieties to TTF, such as perylene diimide 9 or ferrocene. 10 From a general point of view, the association of TTF with coordinating groups within electroactive ligands 11 represents a powerful strategy to access either multifunctional molecular materials, in which a combination of different physical properties can be achieved, 12 or electroactive catalysts. 13 In this respect, nitrogen-containing five-membered rings, such as oxazolines, 14 pyrazoles 15 or imidazoles 16 have been attached to TTF, while the synthesis and coordination chemistry of TTFtriazole ligands has been reported much more recently.…”

Section: Introductionmentioning

confidence: 99%

Tetrathiafulvalene mono- and bis-1,2,3-triazole precursors by click chemistry: structural diversity and reactivity

Cauchy

Avarvari

2014

Org. Biomol. Chem.

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The donor ortho-dimethyl-TTF-(N-n-Bu-1,2,3-triazole) 1,5-isomer has been synthesized by click chemistry following a ruthenium-catalyzed azide-alkyne cycloaddition procedure. The single crystal X-ray analysis showed a planar conformation between the TTF and triazole units and a set of intermolecular interactions at the supramolecular level in the solid state. The same procedure allowed the preparation of the corresponding ortho-dimethyl-TTF-bis(triazole) which was also structurally characterized. Because of the steric hindrance, the triazole units are no longer planar with the TTF backbone. The reactivity of the triazole ring has been investigated in protonation and alkylation reactions, monitored by UV-visible spectroscopy, which clearly showed the red shift of the intramolecular charge transfer band. A TTF-methyl-triazolium salt has been isolated and analyzed by single crystal X-ray analysis. All of the TTF-triazoles and triazolium salts are valuable precursors for radical cation salts due to their oxidation potentials and variety of possible intermolecular interactions.

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Ferrocenyl-triazolyl-tetrathiafulvalene assemblies: synthesis and electrochemical recognition properties

Cited by 11 publications

References 24 publications

Metal-Promoted Intermolecular Electron Transfer in Tetrathiafulvalene–Thiacalix[4]arene Conjugates and Tetrachlorobenzoquinone

Metal-Promoted Intermolecular Electron Transfer in Tetrathiafulvalene–Thiacalix[4]arene Conjugates and Tetrachlorobenzoquinone

Vinylogous Tetrathiafulvalene Based Podands: Complexation Interferences on the Molecular Movements Triggered by Electron Transfer

Tetrathiafulvalene mono- and bis-1,2,3-triazole precursors by click chemistry: structural diversity and reactivity

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