Tetrathiafulvalene chemistry

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Editors: Prof. Peter Skabara and Prof. Marc Sallé
University of Strathclyde and Université Angers
 
Tetrathiafulvalene is a fascinating system: it is quite rare to find a synthetic molecule endowed with such a simple architecture that is capable of concentrating intense interest from various communities of chemists. This success results from the conjunction of intrinsic structural and electronic properties: structurally, this sulfur-rich bicyclic compound is essentially planar (at least in the radical cation state) and therefore presents, as with most of its substituted derivatives, a good propensity to stack in the solid state. This parameter is favorable for efficient charge delocalization in the solid-state and it is this feature that gave birth to the first conducting and superconducting organic salts. This non-aromatic 14 π-electron system is readily oxidized through a reversible process to the corresponding aromatic cation radical and dication species. This excellent π-donating ability, coupled to the high stability of both oxidized species, has contributed to the establishment of this unit as a key contemporary building block for the construction of redoxactive molecular and supramolecular systems.
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Tetrathiafulvalene chemistry

  • Peter J. Skabara and
  • Marc Sallé

Beilstein J. Org. Chem. 2015, 11, 1528–1529, doi:10.3762/bjoc.11.167

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Published 01 Sep 2015

Bis(vinylenedithio)tetrathiafulvalene analogues of BEDT-TTF

  • Erdal Ertas,
  • İlknur Demirtas and
  • Turan Ozturk

Beilstein J. Org. Chem. 2015, 11, 403–415, doi:10.3762/bjoc.11.46

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Published 27 Mar 2015

TTFs nonsymmetrically fused with alkylthiophenic moieties

  • Rafaela A. L. Silva,
  • Bruno J. C. Vieira,
  • Marta M. Andrade,
  • Isabel C. Santos,
  • Sandra Rabaça,
  • Dulce Belo and
  • Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 628–637, doi:10.3762/bjoc.11.71

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Published 05 May 2015

Trifluoromethyl-substituted tetrathiafulvalenes

  • Olivier Jeannin,
  • Frédéric Barrière and
  • Marc Fourmigué

Beilstein J. Org. Chem. 2015, 11, 647–658, doi:10.3762/bjoc.11.73

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Published 06 May 2015

Copper ion salts of arylthiotetrathiafulvalenes: synthesis, structure diversity and magnetic properties

  • Longfei Ma,
  • Jibin Sun,
  • Xiaofeng Lu,
  • Shangxi Zhang,
  • Hui Qi,
  • Lei Liu,
  • Yongliang Shao and
  • Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 850–859, doi:10.3762/bjoc.11.95

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Published 20 May 2015

Tuning of tetrathiafulvalene properties: versatile synthesis of N-arylated monopyrrolotetrathiafulvalenes via Ullmann-type coupling reactions

  • Vladimir A. Azov,
  • Diana Janott,
  • Dirk Schlüter and
  • Matthias Zeller

Beilstein J. Org. Chem. 2015, 11, 860–868, doi:10.3762/bjoc.11.96

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Published 21 May 2015

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

  • Huixin Jiang,
  • Virginia Mazzanti,
  • Christian R. Parker,
  • Søren Lindbæk Broman,
  • Jens Heide Wallberg,
  • Karol Lušpai,
  • Adam Brincko,
  • Henrik G. Kjaergaard,
  • Anders Kadziola,
  • Peter Rapta,
  • Ole Hammerich and
  • Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

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Published 02 Jun 2015

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

  • Sandrina Oliveira,
  • Dulce Belo,
  • Isabel C. Santos,
  • Sandra Rabaça and
  • Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 951–956, doi:10.3762/bjoc.11.106

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Published 03 Jun 2015

Carboxylated dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, electronic properties, and complexation with zinc ions

  • Yunfei Wang and
  • Yuming Zhao

Beilstein J. Org. Chem. 2015, 11, 957–965, doi:10.3762/bjoc.11.107

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Published 03 Jun 2015

Tuning the size of a redox-active tetrathiafulvalene-based self-assembled ring

  • Sébastien Bivaud,
  • Sébastien Goeb,
  • Vincent Croué,
  • Magali Allain,
  • Flavia Pop and
  • Marc Sallé

Beilstein J. Org. Chem. 2015, 11, 966–971, doi:10.3762/bjoc.11.108

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Published 05 Jun 2015

Chiroptical properties of 1,3-diphenylallene-anchored tetrathiafulvalene and its polymer synthesis

  • Masashi Hasegawa,
  • Junta Endo,
  • Seiya Iwata,
  • Toshiaki Shimasaki and
  • Yasuhiro Mazaki

Beilstein J. Org. Chem. 2015, 11, 972–979, doi:10.3762/bjoc.11.109

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Published 08 Jun 2015

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

  • Yoann Cotelle,
  • Marie Hardouin-Lerouge,
  • Stéphanie Legoupy,
  • Olivier Alévêque,
  • Eric Levillain and
  • Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

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Published 17 Jun 2015

Donor–acceptor type co-crystals of arylthio-substituted tetrathiafulvalenes and fullerenes

  • Xiaofeng Lu,
  • Jibin Sun,
  • Shangxi Zhang,
  • Longfei Ma,
  • Lei Liu,
  • Hui Qi,
  • Yongliang Shao and
  • Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 1043–1051, doi:10.3762/bjoc.11.117

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Published 19 Jun 2015

A hybrid electron donor comprising cyclopentadithiophene and dithiafulvenyl for dye-sensitized solar cells

  • Gleb Sorohhov,
  • Chenyi Yi,
  • Michael Grätzel,
  • Silvio Decurtins and
  • Shi-Xia Liu

Beilstein J. Org. Chem. 2015, 11, 1052–1059, doi:10.3762/bjoc.11.118

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Published 22 Jun 2015

Single-molecule conductance of a chemically modified, π-extended tetrathiafulvalene and its charge-transfer complex with F4TCNQ

  • Raúl García,
  • M. Ángeles Herranz,
  • Edmund Leary,
  • M. Teresa González,
  • Gabino Rubio Bollinger,
  • Marius Bürkle,
  • Linda A. Zotti,
  • Yoshihiro Asai,
  • Fabian Pauly,
  • Juan Carlos Cuevas,
  • Nicolás Agraït and
  • Nazario Martín

Beilstein J. Org. Chem. 2015, 11, 1068–1078, doi:10.3762/bjoc.11.120

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Published 24 Jun 2015

Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

  • Flavia Pop and
  • Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

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Published 02 Jul 2015

Advances in the synthesis of functionalised pyrrolotetrathiafulvalenes

  • Luke J. O’Driscoll,
  • Sissel S. Andersen,
  • Marta V. Solano,
  • Dan Bendixen,
  • Morten Jensen,
  • Troels Duedal,
  • Jess Lycoops,
  • Cornelia van der Pol,
  • Rebecca E. Sørensen,
  • Karina R. Larsen,
  • Kenneth Myntman,
  • Christian Henriksen,
  • Stinne W. Hansen and
  • Jan O. Jeppesen

Beilstein J. Org. Chem. 2015, 11, 1112–1122, doi:10.3762/bjoc.11.125

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Published 03 Jul 2015

New tris- and pentakis-fused donors containing extended tetrathiafulvalenes: New positive electrode materials for rechargeable batteries

  • Shintaro Iwamoto,
  • Yuu Inatomi,
  • Daisuke Ogi,
  • Satoshi Shibayama,
  • Yukiko Murakami,
  • Minami Kato,
  • Kazuyuki Takahashi,
  • Kazuyoshi Tanaka,
  • Nobuhiko Hojo and
  • Yohji Misaki

Beilstein J. Org. Chem. 2015, 11, 1136–1147, doi:10.3762/bjoc.11.128

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Published 08 Jul 2015

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

  • Rupert G. D. Taylor,
  • Joseph Cameron,
  • Iain A. Wright,
  • Neil Thomson,
  • Olena Avramchenko,
  • Alexander L. Kanibolotsky,
  • Anto R. Inigo,
  • Tell Tuttle and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

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Published 10 Jul 2015

Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

  • Awatef Ayadi,
  • Aziz El Alamy,
  • Olivier Alévêque,
  • Magali Allain,
  • Nabil Zouari,
  • Mohammed Bouachrine and
  • Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

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Published 07 Aug 2015

Synthesis of racemic and chiral BEDT-TTF derivatives possessing hydroxy groups and their achiral and chiral charge transfer complexes

  • Sara J. Krivickas,
  • Chiho Hashimoto,
  • Junya Yoshida,
  • Akira Ueda,
  • Kazuyuki Takahashi,
  • John D. Wallis and
  • Hatsumi Mori

Beilstein J. Org. Chem. 2015, 11, 1561–1569, doi:10.3762/bjoc.11.172

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Published 08 Sep 2015

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

  • Masahiko Iyoda and
  • Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

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Published 10 Sep 2015

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

  • Alexander L. Kanibolotsky,
  • Neil J. Findlay and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

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Published 28 Sep 2015

[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

  • Laura G. Sarbu,
  • Lucian G. Bahrin,
  • Peter G. Jones,
  • Lucian M. Birsa and
  • Henning Hopf

Beilstein J. Org. Chem. 2015, 11, 1917–1921, doi:10.3762/bjoc.11.207

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Published 15 Oct 2015

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

  • Xiang Sun,
  • Guoqiao Lai,
  • Zhifang Li,
  • Yuwen Ma,
  • Xiao Yuan,
  • Yongjia Shen and
  • Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

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Published 27 Nov 2015
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