Organic electronic conductors and precursors - XII. Synthesis of novel dibenzotetrathiafulvalenes

Persulfurierte Arene sind zwar schon seit etwa 50 Jahren bekannt, ihre Chemie ist aber trotz der einfachen und effizienten Synthesen unter milden Bedingungen nur unzureichend untersucht. Ihre Eigenschaften (Redoxpotentiale, UV/Vis‐Absorption, Leitfähigkeit, nichtlineare optische Eigenschaften) sind einerseits auf die Aromatizität des Rings mit sp2‐hybridisierten Kohlenstoffatomen und andererseits auf den elektronischen Beitrag der divalenten Schwefelsubstituenten zurückzuführen, die auch negative oder positive Ladungen stabilisieren können. Die charakteristischen Konformationsmuster der Schwefelliganden ermöglichen häufig die Präorganisation zu supramolekularen Aggregaten mit oder ohne thiophile Metallkationen. Anwendungen solcher Spezies finden sich in der Entwicklung von Redoxsensoren, ionenselektiven Membranen, Clathraten, organischen Leitern, nichtlinearen optischen Materialien, Flüssigkristallen, Koordinationspolymeren und bioanorganischen Systemen. Darüber hinaus wurde eine neue Klasse von Supermolekülen mit verschiedenen Molekülformen wie Sternen, Ketten, Rädern und Windmühlen beschrieben.

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Persulfurierte aromatische Verbindungen

Gingras

Raimundo

Chabre

2006

Angewandte Chemie

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Persulfurated Aromatic Compounds

2006

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Persulfurated arenes have been known for about 50 years but they were underexploited in chemistry in spite of facile, mild, and high-yielding syntheses. Their properties (redox potentials, UV/Vis absorption, conductivity, nonlinear optical properties, etc.) are mainly due to the aromaticity of the ring with sp2-hybridized carbon atoms and to the electronic contribution from numerous divalent sulfur ligands, which also stabilize negative or positive charges. The characteristic conformational patterns of the sulfur ligands often facilitate preorganization in supramolecular assemblies, with or without thiophilic metal cations, for designing redox sensors, ion-selective membranes, clathrates, organic conductors, nonlinear optical materials, liquid crystals, coordination polymers, and bioinorganic systems. A new class of supramolecules with various molecular shapes such as asterisks, chains, wheels, and windmills were reported.

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ChemInform Abstract: Organic Electronic Conductors and Precursors. Part 12. Synthesis of Novel Dibenzotetrathiafulvalenes.

et al. 1991

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Organic Electronic Conductors and Precursors. Part 12. Synthesis of Novel Dibenzotetrathiafulvalenes.-Treatment of the benzodithiolthiones (Ia) -(Id) and the benzotrisdithioletrione (Ie) with triethyl phosphite results in the formation of the dibenzotetrathiafulvalenes (II). The derivative (IIa) is also prepared by base-promoted ring opening of (IIe) followed by reaction of the octathiolate (III) with methyl iodide. (Cyclic voltammetry of (II), conductivity of some radical cation salts of (IIa) ). -(BEYE, N.; WEGNER, R.; RICHTER, A. M.; FANGHAENEL, E.; Tetrahedron Lett. 32 (1991) 4, 479-482; Dep. Chem., TU, O-4200 Merseburg, Fed. Rep. Ger.; EN)

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Organic electronic conductors and precursors - XII. Synthesis of novel dibenzotetrathiafulvalenes

Cited by 14 publications

References 6 publications

Persulfurierte aromatische Verbindungen

Persulfurierte aromatische Verbindungen

Persulfurated Aromatic Compounds

ChemInform Abstract: Organic Electronic Conductors and Precursors. Part 12. Synthesis of Novel Dibenzotetrathiafulvalenes.

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