Synthesis and Electroconductive Properties of Radical Salts Derived from Tetrathiafulvalene Dimers

Iyoda, Masahiko; Hara, Kenji; Ogura, E.; Takano, Takahiro; Hasegawa, Masashi; Yoshida, Masato; Kuwatani, Yoshiyuki; Nishikawa, Hiroyuki; Kikuchi, Kôichi; Ikemoto, Isao; Mori, Takehiko

doi:10.1006/jssc.2002.9757

Cited by 18 publications

(24 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Iodobenzene, p ‐bromobenzonitrile, p ‐iodoanisole, 2‐bromopyridine, and 2‐bromothiophene reacted with trialkylstannyl‐TTF to produce the corresponding products (Scheme 1a). 2) For the synthesis of bi‐TTFs, Negishi‐type coupling reactions of ZnCl‐TTF with iodo‐TTF derivatives using a palladium (Pd) catalyst have been developed (Scheme 1b) [4] . 3) Sonogashira coupling in the presence of Pd(PPh 3 ) 4 or Pd(PhCN) 2 Cl 2 with CuI as a co‐catalyst has also been developed to produce bis‐TTF acetylene derivatives (Scheme 1c) [5] .…”

Section: Introductionmentioning

confidence: 99%

“…2) For the synthesis of bi-TTFs, Negishi-type coupling reactions of ZnCl-TTF with iodo-TTF derivatives using a palladium (Pd) catalyst have been developed (Scheme 1b). [4] 3) Sonogashira coupling in the presence of Pd(PPh 3 ) 4 or Pd(PhCN) 2 Cl 2 with CuI as a co-catalyst has also been developed to produce bis-TTF acetylene derivatives (Scheme 1c). [5] In 2011, a straightforward synthesis method was developed for aryl TTFs using Pd(OAc) 2 -catalyzed direct CÀ H arylation, which does not require the preparation of metallated precursors (Scheme 1d).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Periphery Modification of Tetrathiafulvalenes: Recent Development and Applications

Yoshimura

Misaki

2021

The Chemical Record

View full text Add to dashboard Cite

Tetrathiafulvalene (TTF) and its analogs are fascinating molecules in materials science based on their excellent electron‐donating abilities. This personal account describes recent advances in the synthesis of TTF analogs for functional materials via the palladium‐catalyzed modification of peripheries of TTF analogs. We first consider three types of molecules: fluorophore‐TTF hybrid molecules, multi‐redox systems, and an organic ligand for metal‐organic frameworks. These molecules were successfully synthesized via Stille coupling or palladium‐catalyzed direct C−H arylation and their structural, electrochemical, and optical properties were clarified. Subsequently, phosphorus‐substituted TTF analogs were successfully synthesized for future applications of redox‐active phosphine ligands for metal catalysts. The development of these molecules can significantly affect the advancement of chemical science.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Periphery Modification of Tetrathiafulvalenes: Recent Development and Applications

Yoshimura

Misaki

2021

The Chemical Record

View full text Add to dashboard Cite

show abstract

“…Thus, the reactions of the tin derivatives 42 and 44 of tetrathiafulvalene (TTF) and tetraselenafulvalene (TSF) produce the bi-TTF 43 (70%) and the bi-TSF 45 (75%) (Scheme 10). [46,47] The reaction of diaryldimethyltins with CuA C H T U N G T R E N N U N G (NO 3 ) 2 also proceeded smoothly in THF at room temperature to afford the biaryls 47a-47d, 31, and 35 in high yields.…”

Section: Copper-mediated Coupling Of Organotin Compoundsmentioning

confidence: 96%

Copper‐Mediated Aryl‐Aryl Couplings for the Construction of Oligophenylenes and Related Heteroaromatics

Iyoda

2009

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

Efficient methods for the syntheses of biaryls by the copper-mediated homocoupling of arylmetals are summarized. First, a smooth transmetallation between arylzinc halides and copper(II) salts has been employed for the selective homocoupling of arylzinc halides to produce either biphenylenes or tetraphenylenes. This reaction has been applied to the synthesis of cyclic oligothiophenes. Second, an efficient method for the homocoupling of aryl halides by the electron-transfer (ET) oxidation of Lipshutz cuprates [Ar 2 Cu(CN)Li 2 ] with organic electron acceptors has been developed. The ET oxidation of cuprates with 1,4-benzoquinones proceeds smoothly to afford the corresponding coupling products in moderate to high yields. The ET oxidation of cuprates has been applied to the synthesis of either thiophene-or benzene-fused 10-membered ring cyclophanes. For the synthesis of macrocyclic cyclophanes, a linear C À Cu À C structure of Lipshutz cuprates should be maintained in the dimetallacyclic intermediates to efficiently produce large-ring cyclophanes. Moreover, nonaphenylenes and dodecaphenylenes have been synthesized using the ET oxidation of cuprates with duroquinone. Interestingly,

show abstract

“…It should be noted that the TMT-bi-TTF compound has already been synthesized by Ullmann coupling from iodo-TTF precursors 11 or transition-metal-catalyzed coupling reactions. 12 Single crystals of TTF1 suitable for X-ray analysis were grown by slow evaporation from 1 : 1 CH 2 Cl 2 : MeOH solution. The X-ray structures obtained confirm the molecular structure of both compounds.…”

Section: Synthesis and Structure Of Ttf1mentioning

confidence: 99%

“…The crystalline structure of the TMT-bi-TTF compound solved in the monoclinic space group P2 1 /n has already been described with crystals obtained from CS 2 solutions. 12 This compound shows polymorphism since crystals obtained from CH 2 Cl 2 : MeOH solutions crystallize in the orthorhombic system, space group Pn2 1 a, with one molecule in the general position. The conjugated system containing the two TTF cores is completely flat and only the methyl groups point out of the plane (Fig.…”

Section: Synthesis and Structure Of Ttf1mentioning

confidence: 99%

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

et al. 2013

View full text Add to dashboard Cite

International audienceIn the search for novel tetrathiafulvalene-substituted dithiolene ligands, two tetrathiafulvalene (TTF) molecules directly connected to 1,3-dithiol-2-one fragments have been synthesized and characterized by single crystal X-ray diffraction, electrochemical and spectroscopic analyses. TTF1 was obtained, in moderate yield, by the cross-coupling of 4,5-bis(methylthio)-1,3-dithiole-2-one with 4,4′-bis(1,3-dithiole-2-one) in triethylphosphite, whereas for TTF2, the 1,3-dithiol-2-one fragment was introduced, in high yield, by an original reaction of the alkyne group of an ethynyl TTF (Me3TTF-C[triple bond, length as m-dash]CH) with xanthogen in the presence of a radical initiator. Opening of the 1,3-dithiol-2-one fragments with sodium methanolate leads to the formation of two new 1,2-dithiolate ligands functionalized with redox-active TTF moieties, which can efficiently coordinate metals. As an illustration, two original heteroleptic bis(cyclopentadienyl)dithiolene titanium complexes were isolated and characterized

show abstract

Synthesis and Electroconductive Properties of Radical Salts Derived from Tetrathiafulvalene Dimers

Cited by 18 publications

References 32 publications

Periphery Modification of Tetrathiafulvalenes: Recent Development and Applications

Periphery Modification of Tetrathiafulvalenes: Recent Development and Applications

Copper‐Mediated Aryl‐Aryl Couplings for the Construction of Oligophenylenes and Related Heteroaromatics

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

Contact Info

Product

Resources

About