Selective stepwise oxidation of 1,4-decamethoxypillar[5]arene

Shurpik, D. N.; Padnya, Pavel L.; Makhmutova, L. I.; Yakimova, Luidmila S.; Stoikov, Ivan I.

doi:10.1039/c5nj01951f

Cited by 25 publications

(31 citation statements)

References 47 publications

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“…1,4-Dimethoxypillar [5]arene (1 a) can be transformed to pillar [5]quinone (3) by the reaction with a high molar excess of a strong oxidizing agent. Cerium ammonium nitrate (CAN) or hypervalent iodine compounds proved to be successful for this reaction (Scheme 1).…”

Section: Pillar[n]quinonesmentioning

confidence: 99%

“…After the pioneering work of Ogoshi and coworkers [1] in 2008 studies on pillar[n]arenes achieved an increasing attraction as macrocyclic host systems. [2] Pillar [5]arenes (1) and pillar [6]arenes (2) are the most important members of this novel class of compounds. In 2009 we found that the 1,4-dialkoxy-substituted benzene rings of this special cyclophane type 1 can be oxidized by cerium ammonium nitrate to 1,4-quinone rings.…”

Section: Introductionmentioning

confidence: 99%

“…In 2009 we found that the 1,4-dialkoxy-substituted benzene rings of this special cyclophane type 1 can be oxidized by cerium ammonium nitrate to 1,4-quinone rings. When all benzene rings in 1 were replaced by 1,4-quinone rings, pillar [5]quinone (3), a pentafold quinone resulted (Figure 1). [3] Figure 2 gives a survey over the possible macrocyclic structures, when m arene rings A (m = 1,2…5) in pillar [5]arenes (1) are transformed to 1,4-quinone rings Q.…”

Section: Introductionmentioning

confidence: 99%

“…When all benzene rings in 1 were replaced by 1,4-quinone rings, pillar [5]quinone (3), a pentafold quinone resulted (Figure 1). [3] Figure 2 gives a survey over the possible macrocyclic structures, when m arene rings A (m = 1,2…5) in pillar [5]arenes (1) are transformed to 1,4-quinone rings Q. Constitutional isomers can exist for m = 2 and 3.…”

Section: Introductionmentioning

confidence: 99%

“…In principle, pillar [6]arenes (2) could lead to 12 different 1,4-quinone derivatives. Although we published in 2009 the first pillar [6]arenes, [3] only a few pillar [5]arene [1]quinones A 5 Q 1 have been obtained until now. Pillar[n-m]arene[m]quinones with n > 6, m = 1,2…are completely unknown.…”

Section: Introductionmentioning

confidence: 99%

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Pillarquinones and Pillararenequinones

Cao

Meier

2018

Israel Journal of Chemistry

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Pillar[n]quinones and pillar [n-m]arene [m]quinones are oxidation products of pillar[n]arenes. Their molecular structure resembles the parent compounds. However, their map of electron density is different. Each 1,4-benzoquinone ring, which replaces a 1,4-dialkoxy-substituted benzene ring decreases the electron density in the interior cavity and increases the electron density on the upper and lower rim of the pillar. The electron donor character is stepwise transformed to an electron acceptor status. This effect alters the complexation tendencies, which are the most interesting properties of these macrocyclic host systems. Figure 1. Pillar[n]arenes and pillar[5]quinone.Figure 2. Pillar[5-m]arene[m]quinones (m = 1-5).

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Section: Pillar[n]quinonesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Pillarquinones and Pillararenequinones

Cao

Meier

2018

Israel Journal of Chemistry

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Overview of the Synthesis and Structure of Calix[n]quinones (n=4, 6, 8)

Cui

Huang

et al. 2020

Chemistry An Asian Journal

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Calix[n]quinones, a class of cyclic oligomers composed of p-benzoquinone structures connected by methylene, have multi-conjugated carbonyl structures and adjustable cavities, which make their synthesis extremely attractive. In this minireview, synthetic methods of calix[n]quinones and recent synthetic experience of our group are summarized. The merits and demerits of various synthetic methods are briefly reviewed as well. When synthesizing calix[n]quinone (n � 6) with a larger ring, the reduction-oxidation method is considered to be the most recommended.

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Long‐Life Pillar[5]quinone Cathode for Aqueous Zinc‐Ion Batteries

Yeşilot,

Solmaz,

Kılıç

et al. 2024

ChemElectroChem

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Aqueous zinc ion batteries (ZIBs) are currently gaining a significant amount of attention as a low‐cost and high safety energy storage option. While mostly inorganic structures are used as cathode materials in aqueous zinc batteries, these materials undergo structural degradation, therefore, alternative organic cathodes are expected to be developed to replace inorganic materials in aqueous zinc ion batteries (AZIBs). In this work, pillar[5]quinone (P5Q) is used as a cathode in AZIBs for the first time. Besides investigating the charge storage mechanism and interfacial property evolution of P5Q by various ex situ analyses, electrochemical quartz crystal microbalance (EQCM) and density functional theory (DFT) demonstrates both Zn2+ and H+ incorporation. The P5Q exhibits >99 % Coulombic efficiency through 10000 cycles at ultra‐fast (500 °C) current density, yielding a capacity value of approximately 120 mAh g−1 at the end of the cycle. When the current density is changed from 500 °C to 120 °C, an initial discharge capacity of approximately 182 mAh g−1 is achieved, demonstrating outstanding performance with over 80 % capacity retention for the subsequent 7000 cycles.

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Selective stepwise oxidation of 1,4-decamethoxypillar[5]arene

Abstract: Pillar[n]arene[m]quinone was synthesized in high yields, and a rule for determining its structure based on the NMR spectra was deduced.

Cited by 25 publications

References 47 publications

Pillarquinones and Pillararenequinones

Pillarquinones and Pillararenequinones

Overview of the Synthesis and Structure of Calix[n]quinones (n=4, 6, 8)

Long‐Life Pillar[5]quinone Cathode for Aqueous Zinc‐Ion Batteries

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