Redox-active proligands from the direct connection of 1,3-dithiol-2-one to tetrathiafulvalene (TTF): syntheses, characterizations and metal complexation

Camerel, Franck; Jeannin, Olivier; Yzambart, Gilles; Fabre, Bruno; Lorcy, Dominique; Fourmigué, Marc

doi:10.1039/c3nj41097h

Cited by 6 publications

(2 citation statements)

References 48 publications

(38 reference statements)

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“…The electronic properties of 3 were investigated by UV–vis absorption spectroscopy in dichloromethane solution. The UV–vis spectra in DCM (Figure S6 in Supporting Information File 1 ) showed π–π* transitions typical of TTF donors [ 21 ], with an intense absorption band centred at approximately at 231 nm and other weaker bands at 269, 305 and 329 nm.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

Oliveira¹,

Belo²,

Santos³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA dissymmetric TTF-type electron donor, cyanobenzene-ethylenedithio-tetrathiafulvalene (CNB-EDT-TTF), was obtained in high yield, by a cross-coupling reaction with triethyl phosphite between 2-thioxobenzo[d][1,3]dithiole-5-carbonitrile and 5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one. This new donor was characterized namely by single crystal X-ray diffraction, cyclic voltammetry, NMR, UV-visible and IR spectroscopy.

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

Oliveira¹,

Belo²,

Santos³

et al. 2015

Beilstein J. Org. Chem.

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“…Surprisingly, discrete complexes resulting from the association of TTF derivative-based ligands and Ti-oxo clusters have been the subject of very few reports . In addition, to the best of our knowledge, no system combining a single Ti(IV) atom associated with one TTF unit has been designed for evaluating the donor–acceptor behavior that could occur between these two entities . Nevertheless, such a type of molecular architecture is highly attractive, as it allows one a priori to deeply investigate and facilitate the understanding of the interaction between the metallic center and the TTF unit upon light excitation, which can then be employed to decipher phenomena observed within multinuclear and/or polymolecular aggregates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Properties of a Titanium(IV)-Tetrathiafulvalene-Based Complex

Casas,

Baudron,

Bonnefont

et al. 2024

Inorg. Chem.

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To deeply investigate the interaction between a tetrathiafulvalene (TTF) unit and a Ti(IV) center, a monomeric heteroleptic octahedral Ti(IV) complex containing a diimine ligand composed of a 1,10-phenanthroline core fused with a TTF fragment (ligand 2a) was prepared. The stable complex formulated as Ti(1) 2 (2a), where 1 is a 2,2′biphenolato derivative, was efficiently synthesized by following a one-step approach. This complex and its model species [Ti(1) 2 (2b)] were fully characterized in solution, and their solid-state structures were established by single-crystal X-ray diffraction analysis. Density functional theory calculations allowed the assignment of the frontier orbitals involved in the electronic transitions characterized by ultraviolet−visible absorption spectroscopy. Electrochemical and spectroelectrochemical studies revealed that the TTF unit within Ti(1) 2 (2a) can undergo two reversible one-electron oxidation processes; a reversible one-electron reduction of the Ti(IV) atom was highlighted. The photophysical measurements performed for this donor−acceptor molecular system indicated that an electron transfer process upon light excitation occurred within Ti(1) 2 (2a).

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Tetrathiafulvalene‐Based Phenanthroline Ligands: Synthesis, Crystal Structures, and Electronic Properties

et al. 2014

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The synthesis and full characterization of three tetrathiafulvalene‐based phenanthroline ligands, namely, N‐(1,10‐phenanthrol‐5‐yl)‐6,7‐(ethylenedithio)tetrathiafulvalene‐2‐carboxamide (1), 2‐[(1,10‐phenanthrol‐5‐yl)aminocarbonylmethylthio]‐3,6,7‐tris(methylsulfanyl)tetrathiafulvalene (2), and 2‐[(1,10‐phenanthrol‐5‐yl)iminomethyl]tetrathiafulvalene (3), are described. The electronic absorption properties and the electrochemical behavior of the three ligands have been studied. The UV/Vis absorption spectra of these compounds have been rationalized by time‐dependent DFT (TD‐DFT) calculations, and the single‐crystal X‐ray structures of 2 and 3 have been determined. The binding properties of these multifunctional systems for various transition metal ions (Ni2+, Zn2+, Cd2+, and Fe2+) have been analyzed in solution by cyclic voltammetry and UV/Vis spectroscopy. The results show that these ligands are suitable candidates for the preparation of electroactive metal complexes and radical cation salts.

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Redox-active proligands from the direct connection of 1,3-dithiol-2-one to tetrathiafulvalene (TTF): syntheses, characterizations and metal complexation

Cited by 6 publications

References 48 publications

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

Synthesis, Characterization, and Properties of a Titanium(IV)-Tetrathiafulvalene-Based Complex

Tetrathiafulvalene‐Based Phenanthroline Ligands: Synthesis, Crystal Structures, and Electronic Properties

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