Development of triarylamine mediator having ionic-tag and its application to electrocatalytic reaction in ionic liquid

Takahashi, Kohta; Furusawa, Takashi; Sawamura, Takahiro; Kuribayashi, Shunsuke; Inagi, Shinsuke

doi:10.1016/j.electacta.2012.05.049

Cited by 21 publications

(12 citation statements)

References 32 publications

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“…Again, to functionalize the external surface of the assembly, we appended aldehyde group in ligand 3 by Vilsmeier–Haack reaction to afford donor 4 (Scheme ). All three donors were characterized by IR, NMR, and HRMS analyses (Figures S1–S7).…”

Section: Resultsmentioning

confidence: 99%

Covalent Postassembly Modification and Water Adsorption of Pd₃ Self-Assembled Trinuclear Barrels

2016

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Three new ditopic imidazole ligands (2-4) were synthesized in high yields and characterized by various spectroscopic techniques. These ligands resulted in the formation of [3 + 6] self-assembled trinuclear barrels (5-7) in quantitative yields by stoichiometric combination of individual ligands and Pd(NO3)2 in DMSO. All the three assemblies (5-7) were characterized by (1)H NMR and ESI-MS analysis, and subsequently, structures of the complexes 5 and 6 were confirmed by single-crystal X-ray diffraction studies. Structure analysis reveals the presence of NO3(-) counteranions in the intermolecular channels/pockets, which could potentially act as H-bonding sites between adsorbed water molecules within the channels. In fact, both the assemblies (5 and 6) showed water uptake (136.58, and 123.78 cm(3) g(-1), respectively) at ambient temperature under maximum allowable humidity. In addition, free aldehyde group present in the bridging ligand in complex 7 provides reactive site for postassembly modification. Herein, Knoevenagel condensation with Meldrum's acid was utilized under mild conditions by targeting aldehyde group appended in prefabricated complex 7 and transformed into a different complex (8) with altered functional group. Such postassembly functionalization enables incorporation of a new functional group without disrupting the integrity of the trifacial structure.

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Section: Resultsmentioning

confidence: 99%

Covalent Postassembly Modification and Water Adsorption of Pd₃ Self-Assembled Trinuclear Barrels

2016

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“…Since in many cases electrochemical partial fluorinations are preferably carried out solvent-free in NEt 3 ÁnHFor NEt 4 FÁnHFtype ionic liquids, 92 triarylamine mediators bearing ionic tags (5 and 6, Fig. 5) have been developed by Fuchigami et al 93 They were successfully employed in electrocatalytic reactions including the deprotection and fluorodesulfurization of dithioacetals. Notably, it was demonstrated that electrolyte and mediator could be recycled after extraction of the product with hexane.…”

Section: Anodic Oxidationmentioning

confidence: 99%

Redox catalysis in organic electrosynthesis: basic principles and recent developments

2014

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Electroorganic synthesis has become an established, useful, and environmentally benign alternative to classic organic synthesis for the oxidation or the reduction of organic compounds. In this context, the use of redox mediators to achieve indirect processes is attaining increased significance, since it offers many advantages compared to a direct electrolysis. Kinetic inhibitions that are associated with the electron transfer at the electrode/electrolyte interface, for example, can be eliminated and higher or totally different selectivity can be achieved. In many cases, a mediated electron transfer can occur against a potential gradient, meaning that lower potentials are needed, reducing the probability of undesired side-reactions. In addition, the use of electron transfer mediators can help to avoid electrode passivation resulting from polymer film formation on the electrode surface. Although the principle of indirect electrolysis was established many years ago, new, exciting and useful developments continue to be made. In recent years, several new types of redox mediators have been designed and examined, a process that can be accomplished more efficiently and purposefully using modern computational tools. New protocols including, the development of double mediatory systems in biphasic media, enantioselective mediation and heterogeneous electrocatalysis using immobilized mediators have been established. Furthermore, the understanding of mediated electron transfer reaction mechanisms has advanced. This review describes progress in the field of electroorganic synthesis and summarizes recent advances.

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“…The original Kaneko condensation 46,47 of 1,4-cyclohexanedione on bis(4-bromophenylamine) led to the dibromotriphenylamine 7 (yield of 65%). This latter underwent a classical Vilsmeier-Haack reaction [48][49][50] affording the trisubstituted triphenylamine 1 with a global yield of 44% (Scheme 3).…”

Section: Synthesismentioning

confidence: 99%

Redox-controlled fluorescence modulation (electrofluorochromism) in triphenylamine derivatives

et al. 2014

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Development of triarylamine mediator having ionic-tag and its application to electrocatalytic reaction in ionic liquid

Cited by 21 publications

References 32 publications

Covalent Postassembly Modification and Water Adsorption of Pd₃ Self-Assembled Trinuclear Barrels

Covalent Postassembly Modification and Water Adsorption of Pd₃ Self-Assembled Trinuclear Barrels

Redox catalysis in organic electrosynthesis: basic principles and recent developments

Redox-controlled fluorescence modulation (electrofluorochromism) in triphenylamine derivatives

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Development of triarylamine mediator having ionic-tag and its application to electrocatalytic reaction in ionic liquid

Cited by 21 publications

References 32 publications

Covalent Postassembly Modification and Water Adsorption of Pd3 Self-Assembled Trinuclear Barrels

Covalent Postassembly Modification and Water Adsorption of Pd3 Self-Assembled Trinuclear Barrels

Redox catalysis in organic electrosynthesis: basic principles and recent developments

Redox-controlled fluorescence modulation (electrofluorochromism) in triphenylamine derivatives

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Product

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Covalent Postassembly Modification and Water Adsorption of Pd₃ Self-Assembled Trinuclear Barrels

Covalent Postassembly Modification and Water Adsorption of Pd₃ Self-Assembled Trinuclear Barrels