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.
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.
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.
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.
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.
Dithiolene dimetallic molybdenum(v) complexes displaying intraligand charge transfer (ILCT) emission
Recatala, David,Gushchin, Artem L.,Llusar, Rosa,Galindo,Brylev, Konstantin A.,Ryzhikov, Maxim R.,Kitamura, Noboru
, p. 12947 - 12955 (2013)
Bifunctional dithiolene ligands have been coordinated to the Mo V(O)(μ-S2)MoV(O) unit to afford [Mo 2O2(μ-S)2(BPyDTS2) 2]2- (12-) (BPyDTS2 (2-bis-(2-pyridyl)methylene-1,3-dithiolene) dianions. Reaction of the 1 2- molybdenum dimer with pentacarbonylchlorothenium(i) affords a tetrametallic complex of formula [Mo2O2(μ-S) 2(BPyDTS2)2{Re(CO)3Cl} 2]2- (22-). The monomeric (CH3) 2Sn(BPyDTS2) (3) tin complex has also been prepared for comparative purposes. In the structure of (Et4N)2[1], the two metal atoms are in a square pyramidal coordination environment defined by two bridging sulfur atoms, one terminal oxygen atom and the two sulfur atoms of the bifunctional dithiolene ligand. This arrangement leaves two nitrogen atoms on each side which coordinate to two Re atoms in the 22- tetrametallic complex. Compound 3 has a distorted tetrahedral structure defined by two carbon atoms of the methyl groups and two sulfur atoms of the dithiolene ligand. The luminescence properties of all three complexes in acetonitrile have been investigated. Detailed studies supported on quantum mechanical calculations revealed that complex 12- shows photoluminescence in the 600-800 nm region with a maximum wavelength of 628 nm and an emission quantum yield of 0.092, associated with an intraligand charge transfer (ILCT) transition. Coordination of two Re(CO)3Cl fragments to 12- to afford 22- does not affect the emission spectrum and shape although it decreases the quantum yield, approximately by a factor of 4.6. Compound 3 exhibits a similar emission spectrum to those of the complexes 12- and 22- in good agreement with the ILCT assignment. The quantum yield of 3 lies between that of the 12- and 22- complexes.