Calixarenes. 24. Complexation by water-soluble calixarenes

Alam, Iftikhar; Gutsche, C. David

doi:10.1021/jo00301a057

Cited by 44 publications

(86 citation statements)

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“…Thus, calix [4]arene has 4 conformers, calix [6]arene has 8, and calix [8]arene can assume up to 16 different conformations 9-11 (see Scheme 1). All these conformers are interconvertible in solution although some conformations are more stable than others.…”

Section: -8mentioning

confidence: 99%

“…In this work, pyrene has been used as a probe and p-tertbutylcalix [4], [6], and [8]arenes as host molecules. Polycyclic aromatic hydrocarbons (PAHs) are well known persistent pollutants with toxic and carcinogenic activity.…”

Section: 141617mentioning

confidence: 99%

“…18 Pyrene is one of the PAHs listed as priority pollutants by the Environmental Protection Agency. 18 In spite of the fact that water soluble calix[n]arenes Scheme 1 (a) Pyrene, the guest molecule used in this work, within p-tert-butylcalix [4]arene in the cone conformation, (b) p-tert-butylcalix [6]arene in the cone conformation and (c) p-tert-butylcalix [8]arene in the 1,2,3,4 alternate cone (or pinched cone) conformation.…”

Section: 141617mentioning

confidence: 99%

“…Pyrene, p-tert-butylcalix [4]arene, p-tert-butylcalix [6]arene, and ptert-butylcalix [8]arene, (all from Aldrich) were used without any purification. Chloroform, ethanol (Merck, Uvasol grade), methanol and acetonitrile (Merck, Lichrosolv) were also used as received.…”

Section: Experimental Materialsmentioning

confidence: 99%

“…[8]arene. This feature is particularly relevant for calix [6]arene, suggesting a very favourable situation for the hydrogen atom abstraction to occur. The analysis of the degradation products revealed the presence of hydroxypyrene as a major photodegradation product for the three hosts.…”

mentioning

confidence: 97%

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Pyrene—p-tert-butylcalixarenes inclusion complexes formation: a surface photochemistry study

Branco

Ferreira

Rego

et al. 2006

Photochem Photobiol Sci

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Diffuse reflectance and luminescence techniques were used to study the photophysics and photochemistry of pyrene within p-tert-butylcalix [n]arenes with n = 4, 6, and 8, and to study their ability to form inclusion complexes in heterogeneous media. Evidences for inclusion complex formation were found for the three hosts under study. [8]arene. This feature is particularly relevant for calix [6]arene, suggesting a very favourable situation for the hydrogen atom abstraction to occur. The analysis of the degradation products revealed the presence of hydroxypyrene as a major photodegradation product for the three hosts. Dihydro-hydroxypyrene was also formed in the case of calix[6]arene and calix [8]arene. The formation of the calixarene's phenoxyl radical and subsequent hydrogen abstraction is consistent with the formation of dihydro-dihydroxypyrene.

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Section: -8mentioning

confidence: 99%

Section: 141617mentioning

confidence: 99%

Section: 141617mentioning

confidence: 99%

Section: Experimental Materialsmentioning

confidence: 99%

mentioning

confidence: 97%

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Pyrene—p-tert-butylcalixarenes inclusion complexes formation: a surface photochemistry study

Branco

Ferreira

Rego

et al. 2006

Photochem Photobiol Sci

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Zinke Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

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This reaction is a one‐pot, three‐step process to treat the mixture of p ‐substituted phenols and formaldehyde under basic conditions to give a group of molecules of high melting points that are primarily composed of cyclic arrays of four phenolic moieties joined by alternating methylene groups attached at positions ortho to the hydroxyl groups, and named these molecules cyclischen mehrkernmethylenephenolverbindungen . This reaction is generally referred to as the Zinke synthesis. This preparative method has subsequently been modified by different groups. In addition, Gutsche coined the name calix[ n ]arene to stand for these molecules. The present study focuses the structural features, modifications and applications of calix[ n ]arene. It has been pointed out that the Zinke–Cornforth procedure in some cases afford calix[4]arenes as major products, whereas Munch's modification can be applied to the synthesis of calix[6]arenes and calix[8]arenes. A lengthy multistep process has also been developed for the preparation of sophisticated calixarene molecules. It has been reported that the cations that complex with calix[ n ]arenes can be divided into two groups, alkali (or alkali‐like). The transition metal cations and the relative orientation of para and phenolic substituents also affects the selectivity of calix[ n ]arenas toward the alkali cations. It has been found that the cone conformer of calix[4]arenas shows the highest affinity for Na + , whereas the partial cone and 1,3‐alternate conformers prefer K + and Cs + . All the known modification methods on calix[ n ]arenas have been discussed, which can be divided into nine groups. Other types of calix[n]arene analogues have been prepared, such as resorcarenes, and homo‐oxacalixarenes. The asymmetric calix[n]arenes are generally obtained by three approaches. The study finds that calixarenes arising from other aldehydes rather than formaldehyde have alkyl or aryl groups at the bridges across the aromatic annulus; and according to the orientation of these substituents, there exist four kinds of stereoisomers. This reaction has very wide applications in the preparation of calix[n]arenes.

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Dreifacher Einschluß durch ein Calixaren: Struktur des Europium(III)‐Komplexes von Bis(homooxa)‐p‐tert‐butylcalix[4]aren

Asfari¹,

Harrowfield

Ogden

et al. 1991

Angewandte Chemie

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Als Minimalmodell für Enzyme kann der dimere Titelkomplex betrachtet werden; die Struktur einer Dimerenhälfte ist rechts abgebildet. Ein EuIII‐Ion (schraffiert) wird im „Boden”︁ des Calixarens von fünf O‐Atomen (gepunktet) koordiniert. Zusätzlich ist ein Dimethylsulfoxid‐Molekül an das EuIII‐Zentrum gebunden und ein Aceton‐Molekül mit eingeschlossen. Der Gedanke an aktives Zentrum, Substrat und Cosubstrat bei Enzymreaktionen liegt nahe.

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Calixarenes. 24. Complexation by water-soluble calixarenes

Cited by 44 publications

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Pyrene—p-tert-butylcalixarenes inclusion complexes formation: a surface photochemistry study

Pyrene—p-tert-butylcalixarenes inclusion complexes formation: a surface photochemistry study

Zinke Synthesis

Dreifacher Einschluß durch ein Calixaren: Struktur des Europium(III)‐Komplexes von Bis(homooxa)‐p‐tert‐butylcalix[4]aren

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