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 27 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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Mitigating Dissolution to Enhance the Performance of Pillar[5]quinone in Sodium Batteries

Adil,

Schmidt,

Vogt

et al. 2024

Batteries & Supercaps

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Sodium‐ion batteries using organic electrode materials are a promising alternative to state‐of‐the‐art lithium‐ion batteries. However, their practical viability is hindered by challenges such as a low specific capacity of the organic electrode materials, or their dissolution in the electrolyte. We herein present a double mitigation strategy to enhance the performance of pillar[5]quinone (P5Q) as positive electrode in sodium batteries. Using 5 M sodium bis(fluorosulfonyl)imide in succinonitrile as highly concentrated electrolyte, and encapsulating P5Q in CMK‐3 (Carbon Mesostructured by KAIST with hexagonally ordered rod‐like carbon domains) as templated ordered mesoporous carbon, we achieve a record cycling performance with improved cycling stability even at elevated temperature (40 °C). The P5Q@CMK‐3 composite electrode delivers 430 mAh g−1 specific discharge capacity at 0.2C rate with 90% retention over 200 cycles. This corresponds to an energy density of 831 Wh kg−1 (based on P5Q mass) and surpasses previous reports on pillarquinones. When operated at 40 °C, the P5Q@CMK‐3 composite electrodes deliver a specific discharge capacity of 438 mAh g−1 with 88% capacity retention over 500 cycles (0.02% per cycle). This study underscores the crucial role the electrolyte plays in advancing organic sodium batteries, offering a promising avenue for the future of sustainable energy technologies.

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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 27 publications

References 47 publications

Pillarquinones and Pillararenequinones

Pillarquinones and Pillararenequinones

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

Mitigating Dissolution to Enhance the Performance of Pillar[5]quinone in Sodium Batteries

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