Dissymmetric calix[4]arenes with C4- and C2-symmetry. Synthesis, x-ray structures, conformational fixation, and proton NMR spectroscopic studies

Andreetti, G. D.; Boehmer, V.; Jordon, J. Graham; Tabatabai, Moniralsadat; Ugozzoli, Franco; Vogt, Walter; Wolff, A.

doi:10.1021/jo00067a040

Cited by 71 publications

(56 citation statements)

References 3 publications

(3 reference statements)

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“…into "forces" a "true" the ligdnd fourfold in the complex symme-R R try,[219b, 240,2411 In the case of tetraester deriva- fold symmetry is also observed in solution at low temperatures and the complex is kinetically (and probably thermodynamically) less stable. [65] This is in agreement with the considerable decrease in the complex formation constants (by more than five orders of magnitude for Na') for the tetraester derivatives of bridged calix [4]arenes (14) when the length of the bridge is reduced from eight to five carbon atoms. [40' The deformation thus caused can no longer be accomodated in the complex.…”

Section: Unmodified Calixarenessupporting

confidence: 75%

Calixarenes, Macrocycles with (Almost) Unlimited Possibilities

Böhmer

1995

Angew. Chem. Int. Ed. Engl.

1,941

882

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The condensation reaction between p‐tert‐butylphenol and formaldehyde leads in a single step to good yields of cyclic oligomers in which, depending on the reaction conditions, either four, six, or eight phenol units are joined by methylene bridges. The beakerlike shape of the most stable conformation of the tetramer has led to their being given the name “calixarenes” (calix = chalice). Resorcinol can undergo condensation in a similar manner with a variety of aldehydes to afford cyclic tetramers with the same basic structure (the resorcarenes). In both cases the reaction does not require the use of dilution techniques, so that large quantities of product can be readily obtained. In addition, the parent compounds can be modified in various ways, in particular at the phenolic hydroxy groups or the phenyl residues; these approaches can be used separately or in combination. Calixarenes are thus ideal starting materials for the synthesis of various types of host molecules and can also act as building blocks for the construction of larger molecular systems with defined structures and functions. Their potential applications range from use as highly specific ligands for analytical chemistry, sensor techniques and medical diagnostics to their use in the decontamination of waste water and the construction of artificial enzymes and the synthesis of new materials for non‐linear optics or for ultrathin layers and sieve membranes with molecular pores.

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Section: Unmodified Calixarenessupporting

confidence: 75%

Calixarenes, Macrocycles with (Almost) Unlimited Possibilities

Böhmer

1995

Angew. Chem. Int. Ed. Engl.

1,941

882

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“…Naphthalene-based macrocycles are relatively rare in the supramolecular literature. 19a , 20 , 22 , 23 , 24 , 25 The large π system is expected to create a macrocycle with a deep or wide cavity; however, most of known naphthalene-based macrocycles often suffer from complicated regioisomeric products with ill-defined and shallow cavities, and rarely show satisfactory guest binding performance.…”

Section: Resultsmentioning

confidence: 99%

Oxatub[4]arene: a smart macrocyclic receptor with multiple interconvertible cavities

et al. 2015

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“…At the time of our serendipitous discovery, there were only two other reports of methylene-bridged macrocyclic naphthalene ring-containing compounds. One was compound 7, which was described in a report by Andreetti et al, 9 and the other was of the cyclic compound 8 which Poh et al 10 reportedly derived from the cyclocondensation of formaldehyde with chromotropic acid. In the case of 8 however, our own research conducted at that time on the chemistry of chromotropic acid with formaldehyde, 1 led us to different conclusions with respect to the putative structure proposed for 8 by Poh ( Figure 4).…”

Section: Introductionmentioning

confidence: 94%

Calixnaphthalenes: Deep, Electron-Rich Naphthalene Ring-Containing Calixarenes. The First Decade.

Georghiou¹,

Li²,

Ashram³

et al. 2005

Synlett

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This Account is dedicated to Professor George Just (McGill University) and to the memory of the late Professors Guido Perold (University of the Witwatersrand) and Satoru Masamune (University of Alberta and M.I.T.) for giving me the initial opportunities to undertake research in chemistry under their guidance; and also to Janette, Melissa, Andreas, Noulla and Menelaos. SYNLETT 2005, No. 6, pp 0879-08910 6 . 0 4 . 2 0 0 5 Advanced online publication: 23.03.2005Abstract: The first naphthalene ring-based analogues of the betterknown and extensively studied calixarenes were synthesized in 1993. Since that time, our group has focused its research on the design and synthesis of other 'calixnaphthalenes'. These endeavours are motivated partly due to the synthetic challenges which they provide, and to the challenges in deciphering their structural and complexation properties. Calixnaphthalenes offer several advantages over their calixarene analogues. Among these are the facts that they can form deeper, more electron-rich and in some cases, chiral, cavities. They also provide a wide range of potential new scaffolds upon which to design and build new receptors for neutral, or charged guest species. Their supramolecular complexation properties have barely been explored as yet since in most cases, only relatively small quantities only of these compounds have been obtained. In this review, all of the known, and previously unreported calixnaphthalenes are described. As well, some of the compounds, which are described, are still subjects of ongoing research.

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Dissymmetric calix[4]arenes with C4- and C2-symmetry. Synthesis, x-ray structures, conformational fixation, and proton NMR spectroscopic studies

Cited by 71 publications

References 3 publications

Calixarenes, Macrocycles with (Almost) Unlimited Possibilities

Calixarenes, Macrocycles with (Almost) Unlimited Possibilities

Oxatub[4]arene: a smart macrocyclic receptor with multiple interconvertible cavities

Calixnaphthalenes: Deep, Electron-Rich Naphthalene Ring-Containing Calixarenes. The First Decade.

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