o-Carborane as an electron-transfer mediator in electrocatalytic reduction

Hosoi, Kohei; Inagi, Shinsuke; Kubo, Tatsuya; Fuchigami, Toshio

doi:10.1039/c1cc12912k

Cited by 62 publications

(51 citation statements)

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“…The catalytic current was observed at ¹1.42 V, and the re-oxidation peak at ¹1.28 V disappeared completely as reported for 1,2-diphenyl-o-carborane, which can mediate the debromination reaction of 1,2-dibromo-1,2-diphenylethane to give stilbene. 6 The foregoing results indicate that the carborane-triphenylamine dyad can effectively work as both anodic and cathodic mediator.…”

Section: Resultsmentioning

confidence: 92%

“…The redox couple of carborane moiety of 1 was negatively shifted from that of 1,2-diphenyl-o-carborane. 6 To provide a more effective understanding for the optical and electrochemical properties, density functional theory (DFT) calculations for 1 and its component molecules were conducted at B3LYP/6-311G+(2d,p)//B3LYP/6-31G(d) level of theory (Fig. 4).…”

Section: Resultsmentioning

confidence: 99%

“…4,5 Recently, we have discovered that 1,2-diphenyl-o-carborane and its ammomium derivative showed clear two reversible redox couples at a negative potential range vs. SCE, and that the second redox couple can mediate electron transfer between glassy carbon cathode and 1,2-dibromo-1,2-diphenylethane very rapidly. 6 Hence, carborane derivatives are now promising candidate for reductive mediator in electrocatalytic reaction.…”

Section: Introductionmentioning

confidence: 99%

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o-Carborane-Triphenylamine Dyad: Studies on Its Acceptor-Donor Behavior toward Dual Redox Mediator

et al. 2013

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Novel carborane-triphenylamine dyad 1 was successfully prepared. The dyad exhibited the aggregation-induced emission (AIE) property in a solution of THF/water [1/99 (v/v)]. The cyclic voltammogram of 1 measured in tetrabutylammonium perchlorate (TBAP)/DMF using glassy carbon (GC) disk working electrode showed redox couples both at anodic side and cathodic side derived from redox responses of the triarylamine and the carborane moieties, respectively. The mediatory behavior of 1 for the anodic oxidation of benzyl alcohol was clearly confirmed by cyclic voltammetry in the presence of 2,6-lutidine. The catalytic current of 1 for the cathodic reduction of 1,2-dibromo-1,2-diphenylethane was also observed.

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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o-Carborane-Triphenylamine Dyad: Studies on Its Acceptor-Donor Behavior toward Dual Redox Mediator

et al. 2013

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“…With regard to the many closo-and nido-carboranes, carborane-based radical anions featuring a 2n+3 electron count are somewhat rare. [8][9][10][11][12][13] In a more recent report on the photophysics of ortho-carboranes with donating arylcarbazolyl substituents it was suggested that the species in their excited states consist of carbazolyl radical cations and radical cluster anions. This assumption was based on absorption spectroscopy where a transient band at 415 nm with a similar spectral profile as the corresponding radical anion was observed 13 (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Electrochemical and spectroelectrochemical studies of C-benzodiazaborolyl-ortho-carboranes

et al. 2013

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. (2013) 'Electrochemical and spectroelectrochemical studies of C-benzodiazaborolyl-ortho-carboranes.', Dalton transactions., 42 (6). pp. 2266-2281.Further information on publisher's website:http://dx.doi.org/10.1039/c2dt32378hPublisher's copyright statement: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. AbstractFifteen C-diazaborolyl-ortho-carboranes, 1-R ′ -2-R ″ -1,2-C 2 B 10 H 10 , where R′ represents the groups 2-(1,3-Et 2 -1,3,2-N 2 BC 6 H 4 )-, 2-(1,3-Ph 2 -1,3,2-N 2 BC 6 H 4 )-, 2-(1,3-Ph 2 -5,6-Me 2 -1,3,2-N 2 BC 6 H 2 )-, 2-(1,3-i Pr 2 -1,3,2-N 2 BC 6 H 4 )-, and 2-(1,3,2-N 2 BC 6 H 6 )-and where R ″ equals to H, Me, Ph, t Bu or SiMe 3 were synthesized. Cyclovoltammetric studies of the compounds showed irreversible oxidation waves which are caused by the oxidation of the heterocycle. Those C-diazaborolyl-ortho-carboranes with Ph, tBu SiMe 3 substituents at the adjacent C-atom of the cage displayed two one-electron reduction waves reflecting the formation of stable radical monoanions with unusual (2n+3) skeletal electron counts. The geometries of these anions were determined by combinations of infrared, UV-visible spectroelectrochemical and computational studies. Additionally the structures of seven new C-diazaborolyl-ortho-carboranes and one new 2-bromo-1,3,2-benzodiazaborole were determined by X-ray crystallography and compared with previously obtained structures.

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“…As shown in Figure 4, their reduction gives rise to two quasireversible closely spaced systems around -1.40 V which can be clearly evidenced on the backward scans of the corresponding time semi-derivative curves (Figure 4b). These are ascribed to the formation of radical anion and dianion species of carborane, [56,57] respectively. Studies with analogous diaryl-substituted ortho-carborane systems have suggested that the electronic charge was located within the carborane cage.…”

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confidence: 99%

Synthesis and electropolymerization of a series of 2,2′-(ortho-carboranyl)bisthiophenes

Zhao

Fabre

Bobadova‐Parvanova

et al. 2017

Journal of Organometallic Chemistry

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A series of 5,5'-functionalized 2,2'-(ortho-carboranyl)bisthiophene with bromo, vinyl, trimethylsilylethyne, N-methylpyrrole or thienyl groups was synthesized and all compounds were characterized by NMR, MS, and X-ray analysis. Electrochemical characterizations of 12a,b and 13a,b were conducted, and the di(thienyl-N-methylpyrrole)-o-carborane 12a and di(bisthienyl)-o-carborane 12b were successfully electropolymerized on a suitable anode to produce the corresponding conducting polymers. DFT calculations are consistent with the electrochemical data.

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o-Carborane as an electron-transfer mediator in electrocatalytic reduction

Cited by 62 publications

References 24 publications

o-Carborane-Triphenylamine Dyad: Studies on Its Acceptor-Donor Behavior toward Dual Redox Mediator

o-Carborane-Triphenylamine Dyad: Studies on Its Acceptor-Donor Behavior toward Dual Redox Mediator

Electrochemical and spectroelectrochemical studies of C-benzodiazaborolyl-ortho-carboranes

Synthesis and electropolymerization of a series of 2,2′-(ortho-carboranyl)bisthiophenes

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