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Burilov, A. R.; Kharitonov, D. I.; Bashmakova, N. I.; Пудовик, М. А.; Коновалов, А. И.

doi:10.1023/a:1020727505464

Cited by 3 publications

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“…Although the synthesis of calix[4]resorcinolarenes with thioamide groups has been reported, there are no reports of the synthesis of calix[4]arenes with thioamide groups on the wide rim. Thioamides 3a−d were synthesized from cyano derivatives 9a−d (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Self-Assembly of Thio Derivatives of Calix[4]arene on Noble Metal Surfaces

Genorio

Meden

et al. 2008

Langmuir

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Self-assembled monolayers (SAMs) provide a simple route to functionalize electrode surfaces with organic molecules. Herein we use cavity-containing derivatives of calix[4]arenes in SAMs. Bound to noble metal surface, the assembled molecules are candidates to serve as molecular sieves for H 2 molecules and H (+) ions, which could have relevance for fuel cell applications. Tetra- O-alkylated calix[4]arenes with thiolacetate and thiolamide wide-rim anchoring groups in cone and partial-cone conformations were designed, synthesized and self-assembled onto Au, Pt, and Pd surfaces. The resulting SAMs were systematically examined. Single crystal X-ray diffraction of 5,11,17,23-tetrakis(thioacetyl)-25,26,27,28-tetra- i-propoxycalix[4]arene confirmed the cone conformation and revealed the cavity dimensions of the SAMs that were formed by immersing noble metal substrates (Au, Pt and Pd deposited on Si-wafers) in solutions of calix[4]arenes. Surface characterization techniques including ellipsometry, cyclic voltammetry (CV) and X-ray photoelectron spectroscopy (XPS) were used, indicating that the metal surface is terminated with a monomolecular layer. Experimental thicknesses obtained from the ellipsometry are consistent with the calculated values. CV results showed 50 to 80% physical passivation against the Fe(CN) 6 (3-/4-) couple, implying an overall relatively low concentration of defects and pinholes in the films. The binding energies of the S2p core level in the XPS were consistent with the literature values and revealed that up to 3.2 out of four anchoring groups were bonded to the noble metal surface.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Self-Assembly of Thio Derivatives of Calix[4]arene on Noble Metal Surfaces

Genorio

Meden

et al. 2008

Langmuir

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“…An exception was the formation of the corresponding ammonium salts [5, 6] and thioamides [7]. Products of nucleophilic replacement of dialkylamino group in the above calix[4]resorcinarenes were not reported.…”

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Synthesis of 3,5-di-tert-butyl-4-hydroxyphenylsulfanylmethyl-substituted tetramethylcalix[4]resorcinarenes

et al. 2010

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SHORT COMMUNICATIONSDialkylaminomethyl-substituted calix[4]resorcinarenes have been reported long ago [1], but further transformations of these compounds were reported in a few publications [2][3][4], and the described transformations did not involve the dialkylaminomethyl group therein. An exception was the formation of the corresponding ammonium salts [5, 6] and thioamides [7]. Products of nucleophilic replacement of dialkylamino group in the above calix[4]resorcinarenes were not reported. On the other hand, deamination of phenolic Mannich bases is their typical reaction [8].Deamination of freshly prepared dialkylaminomethyl-substituted calix[4]resorcinarenes Ia and Ib by the action of 2,6-di-tert-butyl-4-sulfanylphenol (II) resulted in the formation of previously unknown calixarene III containing sterically hindered phenylsulfanyl fragments (yield 68-72%). We also found that the duration of storage of initial compound Ib does not affect the yield of III. By contrast, the reaction of benzenethiol II with calixarene Ia preliminarily stored for 3 months gave a mixture of products of partial replacement of the dimethylamino groups (according to the 1 H NMR data) even after heating for 66 h. The reactivity of calix[4]resorcinarene Ia can be restored after prolonged storage by washing with dimethyl sulfoxide and then with water, followed by drying in air. Presumably, the reactivity of aminomethyl calixarene derivatives Ia and Ib depends on their supramolecular organization.According to [9], molecules of calix[4]resorcinarene Ia in crystal are linked to dimers where dimethylaminomethyl groups of neighboring molecules enter the macroring cavity in each other; therefore, these groups become spatially inaccessible for nucleophilic attack. Such associates are likely to dissociate by the action of solvent, whereas prolonged drying favors the R = Me (a), Et (b).

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Chemistry of calix[4]resorcinarenes

Jain¹,

Kanaiya

2011

Russ. Chem. Rev.

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The review demonstrates the progress in the The review demonstrates the progress in the chemistry of calix[4]resorcinarenes over the last decade. chemistry of calix[4]resorcinarenes over the last decade. Special attention is paid to their synthesis, conformational Special attention is paid to their synthesis, conformational behaviour, functionalization and ability to serve as cavi-behaviour, functionalization and ability to serve as cavitands and capsules, to form monolayers and host ± guest tands and capsules, to form monolayers and host ± guest complexes. Practical applications of calix[4]resorcinarenes complexes. Practical applications of calix[4]resorcinarenes and their derivatives in various fields are surveyed. The and their derivatives in various fields are surveyed. The bibliography includes 296 references bibliography includes 296 references.

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Cited by 3 publications

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Synthesis and Self-Assembly of Thio Derivatives of Calix[4]arene on Noble Metal Surfaces

Synthesis and Self-Assembly of Thio Derivatives of Calix[4]arene on Noble Metal Surfaces

Synthesis of 3,5-di-tert-butyl-4-hydroxyphenylsulfanylmethyl-substituted tetramethylcalix[4]resorcinarenes

Chemistry of calix[4]resorcinarenes

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