One Step Synthesis of Calix[n]quin­ones through the HClO4/PbO2‐Mediated Oxidation of Calix[n]arenes

Lavendomme, Roy; Troian‐Gautier, Ludovic; Zahim, Sara; Reinaud, Olivia; Jabin, Ivan

doi:10.1002/ejoc.201600092

Cited by 8 publications

(11 citation statements)

References 29 publications

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“…TLC‐MS analysis of the solution of S3 plus excess Cu(ClO 4 ) 2 after an NH 4 Cl wash and filtration through a silica pad shows m/z 1177 consistent with the sodium ion of the calixdiquinone, S3‐Q 2 . Oxidative routes to calixdiquinones generally involve thallium or lead reagents and whilst Chung's Fe 3+ sensing by a 1,2,4‐oxadiazole‐substituted calixarene provides precedence for redox mediated, transition metal ion sensing promoting calix[4]diquinone generation, as far as we can tell this work represents the first isolation of a Cu(II) generated calix[4]diquinone.…”

Section: Resultsmentioning

confidence: 99%

Highly Selective Fluorimetric Turn‐Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene‐Based Chemosensors and Chemodosimeters

et al. 2019

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Isoxazolo‐pyrene tethered calix[4]arenes selectively detect copper(II) ions without interference from related perchlorate ions. The fluorescence emission of the probes, synthesised by nitrile oxide alkyne cycloaddition, and characterised by spectroscopic and crystallographic data, is rapidly reduced by Cu(II) ions. Detection limits are in the micromolar or sub‐micromolar range (0.3–3.6 μM) based on a 1 : 1 sensor:analyte interaction. Voltammetric behaviour and 1H NMR data provide new insights into the sensing mechanism which is dependent on the calixarene substitution pattern. When the calixarene lower rim is fully substituted, Cu(II) detection occurs through a traditional chelation mechanism. In contrast, for calixarenes 1,3‐disubstituted on the lower rim, detection takes place through a chemodosimetric redox reaction. The isolation of a calix[4]diquinone from the reaction with excess Cu(ClO4)2 provides confirmation that the sensor–analyte interaction culminates in irreversible sensor oxidation.

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Section: Resultsmentioning

confidence: 99%

Highly Selective Fluorimetric Turn‐Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene‐Based Chemosensors and Chemodosimeters

et al. 2019

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“…In 2015, Lavendomme [22] suggested that PbO 2 and 70% HClO 4 could directly oxidize 3a and 1a-c to the corresponding 2a-c under milder conditions. Scheme 3Employing PbO 2 and 70% HClO 4 as the oxidant, CH 2 Cl 2 / acetone (v/v = 1 : 1) as the solvent, 1a was oxidized to 2a at room temperature, and the yield could reach 42%.…”

Section: One-step Oxidationmentioning

confidence: 99%

“…quinones (n = 4, 6, 8). [22] It mainly includes three steps: diazo coupling, reduction, and oxidation. The calculation results of some yields have been revised and highlighted in Scheme 4.…”

Section: Scheme 3 Pbo 2 /Hclo 4 -Mediated Oxidation Of Calix[n]arenementioning

confidence: 99%

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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“…An alternative method reported for the synthesis of calix [4]quinones from p-t-butylcalixarenes is oxidation with PbO2/HClO4, which has been reported to give similar yields to the thallium trifluoroacetate oxidation method. 14 Calix[4]quinone synthesis has also been reported through electrochemical oxidation. 1 This method does not require chemical oxidising reagents, but can be more difficult to scale up.…”

Section: Introductionmentioning

confidence: 99%

Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone

Cameron

Rajagopalan

Galán

et al. 2019

Supramolecular Chemistry

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The tetrazole-functionalised calixdiquinone 5,17-di-tert-butyl-26,28-bis-(tetrazol-5-ylmethoxy)calix[4]-25,27-diquinone Q was synthesised by chemical oxidation of the bis-tetrazole calix[4]arene precursor using PbO2/HClO4. The single crystal X-ray structure determination of Q confirmed the structure and showed binding of a water molecule in the solid state. Chemical reduction of Q to the dihydroquinone QR was achieved using N,N-diethylhydroxylamine. Comparison of the solution phase photophysical properties of Q or QR in the presence of terbium ions showed significant excitation only with QR, suggesting redox switching of the photophysical response may be possible with this or similar receptors. .

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One Step Synthesis of Calix[n]quinones through the HClO₄/PbO₂‐Mediated Oxidation of Calix[n]arenes

Abstract: A procedure using HClO 4 and PbO 2 allows the straightforward oxidation of para-substituted and unsubstituted calix[n]arenes into the corresponding calix[n]quinones in

Cited by 8 publications

References 29 publications

Highly Selective Fluorimetric Turn‐Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene‐Based Chemosensors and Chemodosimeters

Highly Selective Fluorimetric Turn‐Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene‐Based Chemosensors and Chemodosimeters

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

Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone

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One Step Synthesis of Calix[n]quin­ones through the HClO4/PbO2‐Mediated Oxidation of Calix[n]arenes

Abstract: A procedure using HClO 4 and PbO 2 allows the straightforward oxidation of para-substituted and unsubstituted calix[n]arenes into the corresponding calix[n]quinones in

Cited by 8 publications

References 29 publications

Highly Selective Fluorimetric Turn‐Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene‐Based Chemosensors and Chemodosimeters

Highly Selective Fluorimetric Turn‐Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene‐Based Chemosensors and Chemodosimeters

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

Lanthanoid coordination with a tetrazole-substituted calix[4]diquinone and calix[4]dihydroquinone

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One Step Synthesis of Calix[n]quinones through the HClO₄/PbO₂‐Mediated Oxidation of Calix[n]arenes