New η-electron donors containing two tetrathiafulvalene units fused to 1,4-dithiine and a conducting charge-transfer complex with tetracyanoquinodimethane

Aqad, Emad; Becker, James Y.; Bernstein, Joel; Ellern, Arkady; Khodorkovsky, Vladimir; Shapiro, Lev

doi:10.1039/c39940002775

Cited by 39 publications

(29 citation statements)

References 10 publications

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“…There is a number of bis(TTF) systems closely related to 192 + where the nitrogen atoms are replaced by other heteroatoms, such as S, [257] Te, [258,259] or PPh, [260] but most of these systems have not been investigated in the context of mixed valency. However, Geoffroy and co-workers studied the MV character of radical cations 193 + and 194 + (Scheme 65) by ESR spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

Organic Mixed‐Valence Compounds: A Playground for Electrons and Holes

Heckmann¹,

Lambert²

2011

Angew Chem Int Ed

507

495

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Mixed-valence (MV) compounds are excellent model systems for the investigation of basic electron-transfer (ET) or charge-transfer (CT) phenomena. These issues are important in complex biophysical processes such as photosynthesis as well as in artificial electronic devices that are based on organic conjugated materials. Organic MV compounds are effective hole-transporting materials in organic light emitting diodes (OLEDs), solar cells, and photochromic windows. However, the importance of organic mixed-valence chemistry should not be seen in terms of the direct applicability of these species but the wealth of knowledge about ET phenomena that has been gained through their study. The great variety of organic redox centers and spacer moieties that may be combined in MV systems as well as the ongoing refinement of ET theories and methods of investigation prompted enormous interest in organic MV compounds in the last decades and show the huge potential of this class of compounds. The goal of this Review is to give an overview of the last decade in organic mixed valence chemistry and to elucidate its impact on modern functional materials chemistry.

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Section: Methodsmentioning

confidence: 99%

Organic Mixed‐Valence Compounds: A Playground for Electrons and Holes

Heckmann¹,

Lambert²

2011

Angew Chem Int Ed

507

495

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“…[254] Lçsungsmittelñ [a] Das Radikalanion wurde durch elektrochemische Reduktion mit 0.1 m Tetramethylammonium-tetrafluorophosphat als Leitsalz erzeugt. [254] [b] Geschwindigkeitskonstanten bei 253 K. [254] [257] , Te [258,259] oder PPh [260] + bilden. Diese TTF-Redoxzentren sind hingegen nicht kovalent miteinander verbunden und demzufolge keine MV-Verbindungen im hier verwendeten Sinn.…”

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Organische gemischtvalente Verbindungen: ein Spielplatz für Elektronen und Löcher

2011

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Gemischtvalente (MV) Verbindungen sind ausgezeichnete Modellsysteme, um grundlegende Elektronentransport(ET)‐ und Ladungstransfer(CT)‐Phänomene zu untersuchen. Diese sind in komplexen biophysikalischen Prozessen wie der Photosynthese, aber auch in artifiziellen elektronischen Bauteilen von großer Bedeutung. So sind organische MV‐Verbindungen effiziente Lochtransportmaterialien in organischen lichtemittierenden Dioden (OLEDs), Solarzellen und photochromen Fenstern. Die Bedeutung der organischen gemischtvalenten Chemie sollte jedoch weniger in ihrer direkten Anwendbarkeit gesehen werden, als vielmehr in dem riesigen Kenntnisschatz über Elektronentransferphänomene, der durch ihr Studium gewonnen wurde. Die große Vielfalt an organischen Redoxzentren und Brückeneinheiten, die zu MV‐Verbindungen kombiniert werden können, sowie die stete Weiterentwicklung von ET‐Theorien und ET‐Untersuchungsmethoden förderten das enorme Interesse an organischen MV‐Verbindungen in den letzten Jahrzehnten und zeigen das große Potential dieser Verbindungsklasse auf. Das Ziel dieses Aufsatzes ist es, das letzte Jahrzehnt der organischen gemischtvalenten Chemie zusammenzufassen und ihren Einfluss auf moderne funktionelle Materialien hervorzuheben.

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“…and The Chemical Society of Japan for granting permission to reproduce material within this article that was originally printed in those articles cited in Reference nos. 56,57,65,66,70,73,74,75,76, and 81. I also thank very much the author of these articles.…”

Section: Resultsmentioning

confidence: 99%

“…A semiconducting behavior was observed despite the fact that the salt exhibited a partial degree of charge transfer in both donor and acceptor moieties and a ''fir-tree''-like stacking arrangement of the donor (Fig. 11) with a high density of intra-and interstack S?S contacts (70).…”

Section: Materials Obtained From Bis-ttf Of Type Iia (Macrocyle)mentioning

confidence: 98%