%Mixed Valence Compounds as Probes to Determine the Polarity of 1-Butyl-3-methylimadazolium Ionic Liquids

Ferrer, Belén; García, H.; Schultz, Kevin T.

doi:10.1021/jp0771062

Cited by 6 publications

(4 citation statements)

References 28 publications

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“…[176] MV compounds 23 d + and 31 + , which are both class II systems, were used for a qualitative evaluation of the polarity of ionic liquids. [175] The systematic dependency of the IV-CT band energy on solvent polarity means that MV class II compounds can be used to characterize the polarity of solvents. However, a Hush analysis of the IV-CT bands of these compounds has not yet been published.…”

Section: Mixed-valence Compoundsmentioning

confidence: 99%

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

Heckmann¹,

Lambert²

2011

Angew Chem Int Ed

510

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: Mixed-valence Compoundsmentioning

confidence: 99%

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

Heckmann¹,

Lambert²

2011

Angew Chem Int Ed

510

495

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“…[176] Die MV-Verbindungen 23 d + und 31 + , die Klasse-II-Systeme sind, wurden zur qualitativen Ermittlung der Polaritäten ionischer Flüssigkeiten herangezogen. [175] Aufgrund der systematischen Abhängigkeit der IV-CT-Bandenenergie von der Lçsungsmittelpolarität kçnnen gemischtvalente Klasse-IIVerbindungen zur Charakterisierung von Lçsungsmitteln verwendet werden. Eine Hush-Analyse der IV-CT-Banden dieser Verbindungen wurde jedoch bislang nicht publiziert.…”

Section: +unclassified

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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“…Similar observations were made in an independent study by Shim and Kim,13 who simulated charge transfer between two atoms of a model diatomic solute in 1-ethyl-3-methylimidazolium hexafluorophosphate. These two simulations, together with extensive evidence from solvatochromic studies of ionic liquids, 14,15 including some direct measurements of energies associated with charge-transfer transitions, 16,17 suggest that there is little to distinguish solvation energies in an ionic liquid environment from those found in highly polar conventional solvents such as acetonitrile and dimethyl sulfoxide. This energetic similarity might not be expected to extend to dynamical solvent effects on electron transfer, 18 given the very different time scales and distinct mechanisms of solvation in ionic liquids compared to dipolar solvents.…”

Section: Introductionmentioning

confidence: 97%

Solvent-Controlled Intramolecular Electron Transfer in Ionic Liquids

Chakraborty

Kondo

et al. 2011

J. Phys. Chem. B

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The rates of excited-state intramolecular electron transfer in 9-(4-biphenyl)-10-methylacridinium (BPAc(+)), crystal violet lactone (CVL), and bianthryl have been measured in a variety of ionic liquids using time-correlated single-photon counting. All three of these reactions had previously been studied in conventional dipolar solvents and their reaction rates shown to be controlled by solvation dynamics. The main focus of this work is to ask whether the same relationships between reaction and solvation times already established in dipolar solvents also apply in ionic liquids. In BPAc(+), where reaction conforms to a simple two-state kinetic scheme and reaction rates are easily measured, the result is a clear "yes". In the case of bianthryl, whose spectra reflect the more complex kinetics of a barrierless process, the answer is also yes. In contrast to other recent studies of bianthryl, the present results demonstrate that the same equality between (integral) reaction times and solvation times observed in conventional solvents also applies in ionic liquids. Finally, the case of CVL is less clear due to the greater uncertainty associated with the data afforded by this weak fluorophore, combined with a lack of data in conventional solvents having large solvation times. But the CVL reaction can also be reasonably interpreted as exhibiting a common behavior in dipolar and ionic solvents.

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%Mixed Valence Compounds as Probes to Determine the Polarity of 1-Butyl-3-methylimadazolium Ionic Liquids

Cited by 6 publications

References 28 publications

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

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

Organische gemischtvalente Verbindungen: ein Spielplatz für Elektronen und Löcher

Solvent-Controlled Intramolecular Electron Transfer in Ionic Liquids

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