Synthesis and electrochemistry of self-assembled monolayers containing quinone derivatives with varying electronic conjugation

Trammell, Scott A.; Moore, Martin; Schull, Terence L.; Lebedev, Nikolai

doi:10.1016/j.jelechem.2009.01.023

Cited by 26 publications

(32 citation statements)

References 32 publications

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“…They also synthesized linkers containing single, double and triple bonds, and found that rate constant was the largest for double bond and smallest for single bond. 31,61 Another intriguing aspect of these studies is that at high pH where hydroquinone is deprotonated, rate constant tends to be independent of linker length.…”

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confidence: 99%

The Electrochemical Reaction Mechanism and Applications of Quinones

Kim¹,

Chung²

2014

Bulletin of the Korean Chemical Society

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This tutorial review provides a general account of the electrochemical behavior of quinones and their various applications. Quinone electrochemistry has been investigated for a long time due to its complexity. A simple point of view is developed that considers the relative stability of the reduced quinone species and the values of the first and second reduction potentials. The 9-membered square scheme in buffered aqueous solutions is explained and semiquinone radical stability is discussed in this context. Quinone redox reaction has also been employed in various studies. Diverse examples are presented under three broad categories defined by the roles of quinone: molecular tool for physical chemistry, versatile electron mediator, and charge storage for energy conversion devices.

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confidence: 99%

The Electrochemical Reaction Mechanism and Applications of Quinones

Kim¹,

Chung²

2014

Bulletin of the Korean Chemical Society

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“…The structures of the molecules are shown in Fig. 1B and their synthesis and SAM formation on gold has been reported [19].…”

Section: Introductionmentioning

confidence: 89%

“…The synthesis of the compounds 1, 2 and 3 has been reported [19]. Buffer reagents were purchased from Aldrich and used as received.…”

Section: Methodsmentioning

confidence: 99%

Proton–coupled electron transfer in self-assembled monolayers containing quinone compounds with different bridging groups of varying electronic conjugation

Trammell

Lebedev

2009

Journal of Electroanalytical Chemistry

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“…This protection/deprotection strategy will be illustrated with methyl and silyl protective groups due to their facile electrochemical deprotection [9,31]. Catechol derivatives were immobilized on the microporous Norit carbon by spontaneous reaction with the corresponding diazonium salts and carbon products were characterized by TGA analysis, XPS experiments and nitrogen gas adsorption-desorption measurements in order to provide information about the film composition, as well as the impact of the grafting on the textural properties of the porous carbon.…”

Section: Introductionmentioning

confidence: 99%

Improvement of electrochemical performances of catechol-based supercapacitor electrodes by tuning the redox potential via different-sized O-protected catechol diazonium salts

Touzé

Gohier

Daffos

et al. 2018

Electrochimica Acta

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a b s t r a c tTwo different O-protected catechol diazonium salts were synthetized and reacted with microporous Norit-S50 carbon to investigate the impact of the protecting group on the electrochemical performances of supercapacitor electrodes in 1 M H 2 SO 4 . Carbon products were characterized by thermal gravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS) experiments and nitrogen gas adsorptiondesorption measurements to investigate the film composition, as well as the impact of the grafting on the textural properties of the Norit-S50. Supercapacitor electrodes, prepared from carbon products, were studied by cyclic voltammetry at different scan rates and by galvanostatic charge/discharge experiments after deprotection of catechol-attached groups. It was found that the specific charge was improved by introducing catechol groups under protected forms and that the potential at which the redox reaction occurred depends on the protecting group used. With bulky triisopropylsilyl protecting groups, the formal potential of catechol-attached moieties shifted in the positive direction by about 300 mV, yielding an energy gain significantly increased, compared to the same charge stored in the level of catechol groups introduced with methyl protecting groups. 1100 repetitive charge/discharge curves at 1 A g À1 were achieved to study the stability of supercapacitors electrodes. Results obtained were tentatively explained in terms of the porous structure of the carbon.

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Synthesis and electrochemistry of self-assembled monolayers containing quinone derivatives with varying electronic conjugation

Cited by 26 publications

References 32 publications

The Electrochemical Reaction Mechanism and Applications of Quinones

The Electrochemical Reaction Mechanism and Applications of Quinones

Proton–coupled electron transfer in self-assembled monolayers containing quinone compounds with different bridging groups of varying electronic conjugation

Improvement of electrochemical performances of catechol-based supercapacitor electrodes by tuning the redox potential via different-sized O-protected catechol diazonium salts

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