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Pure Appl. Chem., 1990, Vol. 62, No. 3, pp. 395-406

http://dx.doi.org/10.1351/pac199062030395

Aromatic/quinoid systems: principles and applications

S. Hünig

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  • Molčanov Krešimir, Kojić-Prodić Biserka, Babić Darko, Stare Jernej: Face-to-face stacking of dianionic quinoid rings in crystals of alkali salts of 2,5-dihydroxyquinone in view of π-system polarization. CrystEngComm 2013, 15, 135. <http://dx.doi.org/10.1039/c2ce26119g>
  • Molčanov Krešimir, Kojić-Prodić Biserka, Babić Darko, Žilić Dijana, Rakvin Boris: Stabilisation of tetrabromo- and tetrachlorosemiquinone (bromanil and chloranil) anion radicals in crystals. CrystEngCommun 2011, 13, 5170. <http://dx.doi.org/10.1039/c1ce05513e>
  • Casnati Alessandro, Comelli Emma, Fabbi Massimo, Bocchi Vittorio, Pochini Andrea, Ungaro Rocco, Mori Giovanni, Ugozzoli Franco, Lanfredi Anna Maria Manotti: Synthesis, conformations and redox properties of diametrical calix[4]arenediquinones. Recl Trav Chim Pays-Bas 2010, 112, 384. <http://dx.doi.org/10.1002/recl.19931120613>
  • Suzuki Hiroshi, Kanbara Takaki, Yamamoto Takakazu: Ru(II) complexes with new redox-active 1,10-phenanthroline derivatives: structural, spectral, and electrochemical investigations. Inorg Chim Ada 2004, 357, 4335. <http://dx.doi.org/10.1016/j.ica.2004.06.027>
  • Chonan Takehiro, Takahashi Kazuko: The Synthesis of Difluoro and Dimethyl Derivatives of 2,6-Bis(dicyanomethylene)-2,6-dihydro-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one (CPDT-TCNQ) and the Conducting Properties of the Metallic Salts Based on the Dimethyl Derivative. Bull Chem Soc Jpn 2004, 77, 1487. <http://dx.doi.org/10.1246/bcsj.77.1487>
  • Tarutani Shinji, Takahashi Kazuko: Synthesis, Crystal Structures, and Electrical Properties of Anion Radical Salts of Novel Electron Acceptors, 2,6-Dicyanomethylene-4-oxo-2,6-dihydrocyclopentadithiophene (CPDT-TCNQ) and Its Diselenophene Analogue (CPDS-TCNQ), Having Three Electron-Withdrawing Groups. Bull Chem Soc Jpn 2004, 77, 463. <http://dx.doi.org/10.1246/bcsj.77.463>
  • Handique Jyotirekha G, Baruah Jubaraj B: Conversion of 1,4-naphthalenediol to 1,4-naphthoquinone by 1,4-benzoquinone. Journal of Molecular Catalysis A 2002, 184, 85. <http://dx.doi.org/10.1016/S1381-1169(01)00515-5>
  • Kuz’mina L. G., Perepichka I. F., Perepichka D. F., Howard J. A. K., Bryce M. R.: Supramolecular architecture of two charge-transfer complexes based on 2,7-(X, X)-4,5-dinitro-9-dicyanomethylenefluorenes (X = NO2 or CN) and tetrathiafulvalene. Crystallogr Rep 2002, 47, 251. <http://dx.doi.org/10.1134/1.1466501>
  • TAKEKUMA Shin-ichi, SASAKI Masato, TAKEKUMA Hideko, YAMAMOTO Hiroshi: An Efficient Preparation and Characteristic Properties of Tetramethyl 3,3',3'',3'''-(p-Quinodimethane-7,7,8,8-tetrayl)tetraazulene-1,1',1'',1'''-tetracarboxylate. NIPPON KAGAKU KAISHI 2000, 107. <http://dx.doi.org/10.1246/nikkashi.2000.107>
  • Hünig Siegfried, Kemmer Martina, Meixner Hubert, Sinzger Klaus, Wenner Hermann, Bauer Thomas, Tillmanns Ekkehart, Lux Franz Rudolf, Hollstein Michael, Groß Hans-Georg: 2,5-DisubstitutedN,N′-Dicyanobenzoquinonediimines (DCNQIs): Charge-Transfer Complexes and Radical-Anion Salts and Copper Salts with Ligand Alloys: Syntheses, Structures and Conductivities. Eur J Inorg Chem 1999, 1999, 899. <http://dx.doi.org/10.1002/(SICI)1099-0682(199905)1999:5<899::AID-EJIC899>3.0.CO;2-R>
  • 7,7,8,8-Tetra(2-thienyl)-p-quinodimethanes. New Electron-Donating p-Quinodimehanes. Chem Lett 1999, 519. <http://dx.doi.org/10.1246/cl.1999.519>
  • Starikov E. B.: A comparative three-dimensional Hartree-Fock crystal orbital study of double-stack organic charge-transfer (semi)conductors: TTF-TCNQ, TTF-DCNQI, and TTF-2,5-Me2-DCNQI. Int J Quantum Chem 1998, 66, 47. <http://dx.doi.org/10.1002/(SICI)1097-461X(1998)66:1<47::AID-QUA5>3.0.CO;2-#>
  • Starikov E. B.: Ab initio Hartree-Fock crystal orbital studies on charge-transfer complexes: Different crystal modifications of the same compounds. Int J Quantum Chem 1998, 66, 69. <http://dx.doi.org/10.1002/(SICI)1097-461X(1998)66:1<69::AID-QUA6>3.0.CO;2-Y>
  • Batten Stuart R., Robson Richard: Einander durchdringende Netze: geordnete, periodische Verschlingung. Angew Chem 1998, 110, 1558. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980605)110:11<1558::AID-ANGE1558>3.0.CO;2-7>
  • Erk Peter, Hünig Siegfried, Klebe Gerhard, Metzenthin Tobias, Werner Hermann P., von Schütz Jost- U.: Reversible Redox Systems, LXII. 2,3-Disubstituted 1,4-Benzoquinones and TheirN,N′-dicyanimines: Syntheses, Physical Properties, and CT Complexes with TTF. Liebigs Ann /Recueil 1997, 1997, 1235. <http://dx.doi.org/10.1002/jlac.199719970628>
  • Aonuma Shuji, Sawa Hiroshi, Kato Reizo: Anomalous 13C/15N Isotope Effect in the π-d System (DMe-DCNQI)2Cu Studied by Selective Isotope Substitution. Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals 1996, 285, 163. <http://dx.doi.org/10.1080/10587259608030795>
  • Martín Nazario, Segura JoséL., Seoane Carlos, Torío Cristina, González Araceli, Pingarrón JoséM.: Synthesis of novel chloro-substituted N,N′-dicyanoquinonediimines. Formation of charge transfer complexes and copper radical-anion salts. Synthetic Metal 1994, 64, 83. <http://dx.doi.org/10.1016/0379-6779(94)90279-8>
  • Lu Jia-Xi, Chen Zhi-Da: Novel quasi-aromatic transition metal cluster compounds. Int Rev Phys Chem 1994, 13, 85. <http://dx.doi.org/10.1080/01442359409353291>
  • Erk Peter: Why Do Highly Conducting DCNQI Copper Salts Stay Metallic?. Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals 1994, 242, 91. <http://dx.doi.org/10.1080/10587259408037741>
  • Martin N., Segura J.L., Seoane C., Albert A., Cano F.H.: A novel molecule for the design of organic conductors: 2,5-Bis(3-phenylpropyl)-7,7,8,8-tetracyano-p-quinodimethane. Synthetic Metal 1993, 56, 1730. <http://dx.doi.org/10.1016/0379-6779(93)90315-N>
  • Aonuma Shuji, Sawa Hiroshi, Okano Yoshinori, Kato Reizo, Kobayashi Hayao: Synthesis of DMe-DCNQI-d7 and deuterium-induced metal-insulator transition of (DMe-DCNQI-d7)2Cu. Synthetic Metal 1993, 58, 29. <http://dx.doi.org/10.1016/0379-6779(93)91115-I>
  • Aonuma Shuji, Sawa Hiroshi, Kato Reizo, Kobayashi Hayao: Giant Metal-Insulator-Metal Transition Induced by Selective Deuteration of the Molecular Conductor, (DMe-DCNQI)2Cu (DMe-DCNQI=2,5-dimethyl-N,N'-dicyanoquinonediimine). Chem Lett 1993, 513. <http://dx.doi.org/10.1246/cl.1993.513>
  • Hünig Siegfried, Sinzger Klaus, Jopp Martina, Bauer Dagmar, Bietsch Werner, von Schütz Jost Ulrich, Wolf Hans Christoph: Deuterium-induzierte Phasenumwandlung eines organischen Metalls — ein ungewöhnlicher Isotopeneffekt. Angew Chem 1992, 104, 896. <http://dx.doi.org/10.1002/ange.19921040727>
  • Hünig Siegfried, Sinzger Klaus, Jopp Martina, Bauer Dagmar, Bietsch Werner, von Schütz Jost Ulrich, Wolf Hans Christoph: Deuterium-Induced Phase Transition of an Organic Metal—An Unusual Isotope Effect. Angew Chem Int Ed Engl 1992, 31, 859. <http://dx.doi.org/10.1002/anie.199208591>
  • Günther Erhard, Hünig Siegfried: Mehrstufige reversible Redoxsysteme, LVIII. 2,5-Bis(cyanimino)-2,5-dihydrothieno[3,2-b]thiophene – ein neuer Acceptortyp: Synthese und allgemeine Eigenschaften. Chem Ber 1992, 125, 1235. <http://dx.doi.org/10.1002/cber.19921250533>
  • Günther Erhard, Hünig Siegfried, Schütz Jost-Ulrich Von, Langohr Uwe, Rieder Harald, Söderholm Svante, Werner Hans-Peter, Peters Karl, Schnering Hans Georg Von, Lindner Hans Jörg: Mehrstufige reversible Redoxsysteme, LIX. Leitfähige Charge-Transfer-Komplexe von 2,5-Bis(cyanimino)-2,5-dihydrothieno[3,2-b]thiophenen mit organischen Donoren. Chem Ber 1992, 125, 1919. <http://dx.doi.org/10.1002/cber.19921250820>
  • Erk Peter, Meixner Hubert, Metzenthin Tobias, Hünig Siegfried, Langohr Uwe, von Schütz Jost U., Werner Hans-Peter, Wolf Hans C., Burkert Rainer, Helberg Hans W.: A guidance for stable metallic conductivity in copper salts ofN,N-dicyanobenzoquinonediimines (DCNQIs). Adv Mater 1991, 3, 311. <http://dx.doi.org/10.1002/adma.19910030610>
  • Ermer Otto: Sevenfold diamond structure and conductivity of copper dicyanoquinonediimines Cu(DCNQI)2. Adv Mater 1991, 3, 608. <http://dx.doi.org/10.1002/adma.19910031208>
  • Almen Hartmut, Bauer Thomas, Hünig Siegfried, Kupčik Vladimir, Langohr Uwe, Metzenthin Tobias, Meyer Klaus, Rieder Harald, von Schütz Jost Ulrich, Tillmanns Ekkehart: Benzol-bis(diazocyanide) - die ersten Acceptoren vom inversen Wurster-Typ für leitfähige organische Materialien. Angew Chem 1991, 103, 608. <http://dx.doi.org/10.1002/ange.19911030534>
  • Erk Peter, Hünig Siegfried, Klebe Gerhard, Krebs Martin, Schütz Jost Ulrich Von: Mehrstufige reversible Redoxsysteme, LVI. Kristallstruktur und Leitfähigkeiten der CT-Komplexe TTF/2-X-5-Me-DCNQI (X = Cl, Br, I) aus Tetrathiafulvalen und 2-Halogen-N,N′-dicyan-5-methyl-1,4-benzochinondiimin. Chem Ber 1991, 124, 2005. <http://dx.doi.org/10.1002/cber.19911240921>
  • Hünig S., Erk P., Günther E., Meixner H., Metzenthin T., von Schütz J.U., Bair M., Groß H.-J., Langohr U., Söderholm S.: Acceptors of the DCNQI type. Recent results and new developments. Synthetic Metal 1991, 42, 1781. <http://dx.doi.org/10.1016/0379-6779(91)91951-6>
  • Hünig S., Sinzger K., Langohr U., Rieder H., Söderholm S., von Schütz J.-U., Wolf H.C.: Radical anion salts and charge-transfer complexes of bridged DCNQIS. Synthetic Metal 1991, 42, 1823. <http://dx.doi.org/10.1016/0379-6779(91)91959-E>
  • Kobayashi Keiji, Mazaki Yasuhiro, Kikuchi Koichi, Saito Kazuya, Ikemoto Isao, Hino Shojun: Novel Conducting Copper Complexes Based on Thiophene-fused DCNQI. Chem Lett 1991, 1033. <http://dx.doi.org/10.1246/cl.1991.1033>