Acid-catalysed synthesis of a new class of calix[4]arenes

Sartori, Giovanni; Maggi, Raimondo; Bigi, Franca; Arduini, Arturo; Pastorio, Andrea; Porta, Cecilia

doi:10.1039/p19940001657

Cited by 42 publications

(19 citation statements)

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“…Recently, Sartori et al described the first example of a calix [4]arene in which two distal methylene bridges are substituted by aryl rings. 8 Such substit- † The Hebrew University of Jerusalem. ‡ Johannes-Gutenberg-Universität.…”

Section: Introductionmentioning

confidence: 99%

“…2 Derivatization reactions usually involve the phenolic hydroxy groups (acylation, alkylation or even elimination or replacement), the p-positions (all kinds of electrophilic substitution, eventually after elimination of the tert-butyl groups), or the phenolic units as a whole (oxidation to p-quinones and subsequent reactions). Numerous selective procedures, involving certain phenolic units, are available not only in the calix- [4]arene 3 series, but increasingly also for calix [6]arenes 4 and more recently even for calix [5]-5 and calix [8]arenes. 6 Another possible modification of the calixarene skeleton involves the methylene bridges, which however are not as easily amenable to chemical reactions.…”

Section: Introductionmentioning

confidence: 99%

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Alkanediyl Bridged Calix[4]arenes: Synthesis, Conformational Analysis, and Rotational Barriers

et al. 1996

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In calix [4]arenes when one methylene bridge carries an alkyl or aryl substituent, two diastereomeric cone conformations are possible in which this substituent assumes the equatorial or axial position. Two diastereomers with cis or trans arrangement of the substituents exist for the corresponding compounds with two substituted bridges, and diastereomeric cone conformations have to be considered additionally in most cases. Molecular mechanics calculations predict an energetical preference of the equatorial position of the substituents in both systems. This preference is markedly more pronounced for alkyl groups than for aryl groups. To test these predictions a series of calix[4]arenes in which one (4) or two opposite (5) methylene bridges are substituted by alkyl or aryl groups was synthesized by fragment condensation. For these calixarenes the solution conformations, the equatorial/axial conformational equilibria, and the energy barriers for the cone to cone ring inversion were determined by 1 H NMR spectroscopy. The experimental energy differences between the two cone conformations correlate well with the calculated ones. Free energies of activation ∆G q for the cone to cone ring inversion of the monoalkyl substituted compounds 4 increase in the order methyl < tert-butyl < ethyl < isopropyl. For the bisalkyl substituted compounds (5b-d) only the cis-isomer could be isolated while cis-and trans-isomers were obtained for 5a and for the bisaryl compounds 5e-g. Among the cis-isomers 5a-d exist exclusively as the equatorial conformers, while the conformational equilibrium is strongly solvent dependent for 5e-g. Single crystal X-ray structures were obtained for several calixarenes with one (4b) or two substituted bridges (5e-g). Here the substituents are found exclusively in the equatorial position, and the molecular conformation is similar to the calculated one.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Alkanediyl Bridged Calix[4]arenes: Synthesis, Conformational Analysis, and Rotational Barriers

et al. 1996

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“…Görmar等 [46] 此方法首先由Böhmer等 [48,49] 和Sartori等 [50] 提出. Sar-tori等 [50] . 片段缩合方法也被陈传峰等 [52,53] 在2009年成功应用于制备含有三联苯结构的杯 [6]芳烃衍生物.…”

Section: 得到单取代的衍生物unclassified

<italic>Meso</italic> position functionalized calix[<italic>n</italic>]arenes and pillar[<italic>n</italic>]arenes and their applications

Zhang¹,

Zuo²,

Wang³

et al. 2020

Sci. Sin.-Chim

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With the rapid development of macrocyclic chemistry, the functionalization of calix[n]arenes, pillar[n]arenes and other methylene linked macrocycles at their meso positions has drawn much attention. These modified macrocyclic derivatives have new functions on the basis of not changing their original properties. Not only more functional groups can be introduced, but also their applications, such as drug delivery, chemical detection, fluorescent system fabrication, are further improved due to the self-assembly behavior of host and guest. Based on the comprehensive analysis of the current research on the modification of calix[n]arenes and pillar[n]arenes at meso position, this review systematically summarizes the modification methods, the changes of the modified structures, and applications. The opportunities and challenges of its future development have been discussed.

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“…Synthetic access to C [4]s that deviate from classical methylene bridge composition (i.e. those that contain ≥1 different bridge) has been known for some time (32)(33)(34)(35)(36)(37). Elegant work by the Böhmer and Biali groups (amongst others) detailed the synthesis of such species through the use of stepwise and fragment condensation methods.…”

Section: Figure 1 -Please See End Of Manuscriptmentioning

confidence: 99%

Investigations into cluster formation with alkyl-tethered bis-calix[4]arenes

Coletta

McLellan

Cols

et al. 2016

Supramolecular Chemistry

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Investigations into cluster formation with alkyl-tethered biscalix[4]arenes Abstract: Calix[4]arenes are versatile ligands capable of forming a wide range of cluster motifs when reacted with 3d, 4f or 3d/4f metal ions. Synthetic modification at the calix[4]arene methylene bridge offers a unique opportunity to explore cluster formation with these alternative building blocks. Here we present the synthesis of a range of bis-calix[4]arenes that are tethered by alkyl chains, as well as exploratory structural studies into cluster-forming reactions. Single crystals were formed in four cases, and from the X-ray structures elucidated it is possible to conclude that sufficiently long alkyl tethers allow for the formation of established cluster topologies without disruption to the core coordination chemistry.

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Acid-catalysed synthesis of a new class of calix[4]arenes

Cited by 42 publications

References 8 publications

Alkanediyl Bridged Calix[4]arenes: Synthesis, Conformational Analysis, and Rotational Barriers

Alkanediyl Bridged Calix[4]arenes: Synthesis, Conformational Analysis, and Rotational Barriers

<italic>Meso</italic> position functionalized calix[<italic>n</italic>]arenes and pillar[<italic>n</italic>]arenes and their applications

Investigations into cluster formation with alkyl-tethered bis-calix[4]arenes

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Acid-catalysed synthesis of a new class of calix[4]arenes

Cited by 42 publications

References 8 publications

Alkanediyl Bridged Calix[4]arenes: Synthesis, Conformational Analysis, and Rotational Barriers

Alkanediyl Bridged Calix[4]arenes: Synthesis, Conformational Analysis, and Rotational Barriers

&lt;italic&gt;Meso&lt;/italic&gt; position functionalized calix[&lt;italic&gt;n&lt;/italic&gt;]arenes and pillar[&lt;italic&gt;n&lt;/italic&gt;]arenes and their applications

Investigations into cluster formation with alkyl-tethered bis-calix[4]arenes

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<italic>Meso</italic> position functionalized calix[<italic>n</italic>]arenes and pillar[<italic>n</italic>]arenes and their applications