132765-35-6Relevant articles and documents
Synthesis and nanostructures of several tetrathiafulvalene derivatives having the side chains composed of chiral and hydrogen-bonding groups and their charge-transfer complexes
Tatewaki, Yoko,Watanabe, Takanori,Watanabe, Koji,Kikuchi, Kohei,Okada, Shuji
, p. 16121 - 16127 (2013)
Tetrathiafulvalene (TTF) derivatives TTF-Bor, TTF-2UM and TTF-4UM having chiral urethane groups were prepared. Among them, TTF-2UM, TTF-4UM and their charge-transfer (CT) complexes with F4TCNQ organized the nanowires. The intermolecular hydrogen bonding of the chiral urethane groups and π-stacking of TTF moieties or the formation of CT complexes resulted in a long one-dimensional nanowires. The chiral moieties were responsible for the molecular orientation of TTF cores to give helical structures. Electronic conductivity of the films of nanowires composed of TTF-2UM and TTF-4UM with F4TCNQ were determined to be 8.0 × 10-2 and 3.2 × 10-2 S cm-1, respectively.
Fabrication and operation of monolayer mott FET at room temperature
Yang, Fan,Suda, Masayuki,Yamamoto, Hiroshi M.
, p. 1259 - 1266 (2017)
Self-assembled monolayer FET based on a TTF derivative is described (FET = field-effect-transistor, TTF = tetrathiafulvalene). The molecule is anchored on an alumina dielectric layer through covalent bonding of a phosphonic acid linker. A p-type monolayer FET device is achieved and subsequent chemical doping of this monolayer with F4TCNQ dopants results in an ambipolar device. (F4TCNQ = 2,3,5,6-Tetrafluoro- 7,7,8,8-tetracyanoquinodimethane) Several strange behaviors including a gate voltage shift upon doping seem to be consistent with organic monolayer Mott FET. Finally, temperature dependence of the FET performance, which also fit the anticipated Mott FET behavior, is discussed.
The chemistry of TTFTT; 1: New efficient synthesis and reactions of tetrathiafulvalene-2,3,6,7-tetrathiolate (TTFTT): An important building block in TTF-syntheses
Svenstrup,Rasmussen,Hansen,Becher
, p. 809 - 812 (1994)
An improved and efficient synthesis of tetrathiafulvalene-2,3,6,7-tetrathiolate (TTFTT) 5 is reported. TTF-tetrathiolate 5 was generated from 2,3,6,7-tetrakis(2'-cyanoethylthio)tetrathiafulvalene (11) under basic conditions at room temperature and was subsequently reacted with a range of electrophiles giving improved synthesis of known systems as well as new TTF-derivatives in excellent yields.
Bis(trisubstituted tetrathiafulvalenyl) disulfides: Disulfide-bridged TTF dimers
Leriche, Philippe,Giffard, Michel,Riou, Amedee,Majani, Jean-Philippe,Cousseau, Jack,Jubault, Michel,Gorgues, Alain,Becher, Jan
, p. 5115 - 5118 (1996)
The title compounds are synthesized, using the oxidative coupling of TTF thiolates. The disulfide linkage induces approximate orthogonality between the two TTF units, while maintaining virtually unchanged their electrochemical properties.
New tetrathiafulvalenes containing carbazole and 1,3,5-triazine fragments: Synthesis, electro-chemical and optical properties
Ignatenko,Gorbunov,Shklyaeva,Abashev
, p. 691 - 698 (2014)
New tetrathiafulvalenes, containing carbazole and 1,3,5-triazine fragments added to the tetrathia-fulvalene ring by means of a S-CH2-CH 2-O bridge, were synthesized. The electrochemical properties of the initial compounds and of the final products were investigated by cyclic voltammetry. The optical characteristics of their solutions were studied by UV absorption spectroscopy and fluorescence spectroscopy.
Chiral EDT-TTF precursors with one stereogenic centre: Substituent size modulation of the conducting properties in the (R-EDT-TTF)2PF6 (R = Me or Et) series
Mroweh, Nabil,Auban-Senzier, Pascale,Vanthuyne, Nicolas,Canadell, Enric,Avarvari, Narcis
, p. 12664 - 12673 (2019)
Modulation of the packing of the donors in the solid state and of the conducting behaviour is achieved in chiral radical cation salts based on the mono-alkylated donors methyl-ethylenedithio-tetrathiafulvalene (Me-EDT-TTF 1) and ethyl-ethylenedithio-tetrathiafulvalene (Et-EDT-TTF 2), underlining the paramount role of the number of stereogenic centres and substituent steric hindrance. Both donors have been prepared as racemates and then separated as pure enantiomers by chiral HPLC. Electrocrystallization experiments provided two complete series of crystalline radical cation salts formulated as [(R)-1]2PF6, [(S)-1]2PF6, and [(rac)-1]2PF6 and [(R)-2]2PF6, [(S)-2]2PF6 and [(rac)-2]PF6·(THF), respectively. The mixed valence salts of 1 show metal-like conductivity in the high temperature regime, while the radical cation salts of 2 are semiconductors, with a much higher conductivity for the enantiopure compounds than the racemic one. Tight-binding band structure calculations of the extended Hückel type performed for all the materials explain the observed conducting behaviour and show the differences in the intermolecular interactions triggered by the change of substituent between 1 and 2.
Donor/acceptor interactions in self-assembled monolayers and their consequences on interfacial electron transfer
Pacsial, Eden J.,Alexander, Daniel,Alvarado, Robert J.,Tomasulo, Massimiliano,Raymo, Francì§isco M.
, p. 19307 - 19313 (2004)
The supramolecular association of tetrathiafulvalene (TTF) donors and bipyridinium acceptors is employed routinely to direct the formation of host/guest complexes and interlocked molecules in bulk solution. We have reproduced these donor/acceptor interactions at electrode/solution interfaces and demonstrated their pronounced influence on heterogeneous electron transfer. Specifically, we have synthesized a TTF with an oligomethylene arm terminated by a thiol group and assembled monolayers of this compound on gold. We have observed that the cyclic voltammogram of the immobilized TTF donors varies significantly upon addition of benzyl viologen, tetracyanoquinodimethane (TCNQ), or tetracyanoethylene (TCNE) acceptors to the electrolyte solution. Indeed, the supramolecular association of the complementary donors and acceptors results in a pronounced current decrease for the TTF redox waves. Consistently, the electrochemical response of the acceptors changes dramatically in the presence of TTF donors on the electrode surface. Instead, hexadecanethiolate monolayers, lacking the TTF donors at the termini of the oligomethylene chains, have a marginal influence on the voltammograms of the acceptors. Impedance measurements indicate that the charge-transfer resistance (RCT) for the reduction of the acceptors increases from less than 0.3 k?, at bare gold, to 324, 24, and 43 k? for benzyl viologen, TCNQ, and TCNE, respectively, at TTF-coated electrodes. By contrast, the electrode coating has a negligible influence on the cyclic voltammogram and impedance response of ferrocene, which cannot sustain donor/acceptor interactions with the immobilized TTFs. Thus, our results demonstrate that the interfacial complexation of complementary donors and acceptors has a dramatic effect on the heterogeneous electron transfer to and from the associated components.
New π-extended donors: Synthesis, characterization, electrochemical and electrical conductivity studies
Zitouni, Amel,Gouasmia, Abdelkrim,Bouguessa, Sabrina,Kaboub, Lakhemici,Boudiba, Louiza
, p. 1744 - 1754 (2011)
A new series of tetrathiafulvalene (TTF) molecules with extended π-system was prepared by using a Wittig reaction to generate the TTF key. The process of deprotection-alkylation of thiolates provided access to a wide variety of molecules. The study of the
Luminescence switching of a cyclometalated iridium(III) complex through a redox-active tetrathiafulvalene-based ligand
Xu, Chun-Hu,Sun, Wei,Zhang, Chao,Zhou, Can,Fang, Chen-Jie,Yan, Chun-Hua
, p. 8717 - 8721 (2009)
A tetrathiafulvalene (TTF) moiety through an acetyl acetonate bridge to a phosphorescent Iridium (Ir) core with a luminescent active MLCT excited state to observe redox controlled electronic coupling between the inorganic metal luminophore and TTF spacer through distinct luminescent behaviours has been reported. The TTF structure was confirmed by mass spectrometry and NMR spectrocopy. The phosphorescence property of complexes can be modulated by ET-acac ligand, which exhibits different photo-induced electron transfer efficiencies of TTF in distinct oxidation states. The target compound may serve as a novel model compound to investigate the mechanism of charge transfer between Ir based luminescent layer and conductive layer, such as derivative, in OLED materials. The singlet-triplet interactions at excited states contribute to the dynamic π-d coupling in TTF-based metal compounds.
New tetrathiafulvalenes containing a 2,5-bis(thiophen-2-yl)pyrrole fragment: Synthesis, optical properties, and electrochemical behavior
Ignatenko,Shklyaeva,Abashev
, p. 1379 - 1385 (2013)
The reaction of 1-(3-bromopropyl)-2,5-bis(thiophen-2-yl)-1H-pyrrole with cesium 5-methylsulfanyl-2-thioxo-1,3-dithiole-4-thiolate generated in situ gave previously unknown 4-{3-[2,5-bis(thiophen-2-yl)-1H-pyrrol-1-yl]propylsulfanyl}- 5-methylsulfanyl-1,3-dithiole-2-thione, and cross-coupling of the latter with 4,5-disubstituted 1,3-dithiole-2-thiones in the presence of triethyl phosphite afforded new substituted tetrathiafulvalenes containing a 2,5-bis(thiophen-2-yl) pyrrole fragment. Optical properties and electrochemical behavior of the synthesized compounds were studied, and their ability to undergo electropolymerization was confirmed.
