Azacalixarene: A New Class in the Calixarene Family

Tsue, Hirohito; Ishibashi, Koichi; Tamura, Rui

doi:10.1007/7081_2007_094

Cited by 133 publications

(108 citation statements)

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“…[7] After our numerous attempts to prepare azacalix [6]arene 2, a convergent 5+1 fragment-coupling approach, as shown in Scheme 1, was finally devised. The 5-fragment 5 was prepared in 92 % yield by the full N-benzylation of liner pentamer 4.…”

Section: Resultsmentioning

confidence: 99%

“…In recent years, nitrogen-bridged calixarene analogues have emerged as a new calixarene family. [7] While the diversity is still limited relative to those of carbon-and sulfur-bridged calixarenes, intriguing complexation properties based on the introduction of nitrogen atoms as the bridging units have thus far been disclosed. [8][9][10] For instance, Wang reported that azacalix [m]arene[n]pyridines exhibited much greater complexation ability for fullerenes C 60 and C 70 , relative to those of other mono-macrocyclic receptors reported to date.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3] As typified by thiacalixarenes, a variety of calixarene analogues with heteroatoms as the bridging units have thus far been reported. [3][4][5][6][7] Interest in these analogues comes from the fact that replacement of the carbon bridges with heteroatoms can impart novel properties and functions to the molecules. In recent years, nitrogen-bridged calixarene analogues have emerged as a new calixarene family.…”

Section: Introductionmentioning

confidence: 99%

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Azacalix[6]arene Hexamethyl Ether: Synthesis, Structure, and Selective Uptake of Carbon Dioxide in the Solid State

Tsue

Ishibashi

Tokita

et al. 2008

Chemistry A European J

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To investigate dynamic solid-state complexation hitherto unexplored in nitrogen-bridged calixarene analogues, azacalix[6]arene hexamethyl ether has been prepared in three steps by applying a 5+1 fragment-coupling approach by using a Buchwald- Hartwig aryl amination reaction with the aid of our previously devised temporal N-silylation protocol. X-ray crystallographic analysis and NMR spectroscopic measurements have revealed that the azacalix[6]arene is well endowed with hydrogen-bonding ability, by which both the molecular and crystal structures are controlled. The azacalix[6]arene is conformationally flexible in solution on the NMR time scale, whereas it adopts a definite 1,2,3-alternate conformation with S2 symmetry in the solid state as a result of intramolecular bifurcated hydrogen-bonding interactions. In the crystal, molecules of the azacalix[6]arene are mutually interacted by intermolecular hydrogen bonds to establish one-dimensional hexane-filled nanochannel crystal architecture. Although the single crystal was broken after desolvation, the resultant polycrystalline powder material was capable of selectively adsorbing CO2 among the four main gaseous components of the atmosphere. In contrast, carbocyclic p-tert-butylcalix[6]arene hexamethyl ether, the crystal structure of which was also elucidated for the first time in the present study, gave rise to almost no uptake of CO2. Additional solid-gas adsorption experiments for another three gases, such as N2, O2, and Ar, suggested that quadrupole/induced-dipole interactions and/or hydrogen-bonding interactions played an important role in permitting the observed selective uptake of CO2 by this new azacalix[6]arene in the solid state.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Azacalix[6]arene Hexamethyl Ether: Synthesis, Structure, and Selective Uptake of Carbon Dioxide in the Solid State

Tsue

Ishibashi

Tokita

et al. 2008

Chemistry A European J

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“…[21,22] Heteroatom-bridged calix(het)arenes, also known as heterocalixaromatics, have gained considerable attention in recent years, because of their easy accessibility, tunable conformational structures, and versatile molecular recognition properties. [7,[23][24][25] Although combinations of diverse aromatic rings and heteroatoms can generate in theory numerous macrocyclic compounds, most studies have been focused on calix [4]arenes macrocycles which contain four aromatic rings bridged by heteroatoms. [26,27] The smallest macrocycles in the family are the less investigated heterocalix [3]arenes, most of them having a C 3 -symmetry, which are also attractive compounds for use in host-guest and supramolecular chemistry.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and inclusion properties of boroncalix[3]arene compounds obtained by self‐assembly of 3‐aminophenylboronic acid and salicylaldehyde derivatives

González‐Hernández

Serrano‐Melgar

Villamil‐Ramos

et al. 2017

Heteroatom Chemistry

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The syntheses, characterization, and inclusion properties of two new trinuclear boron compounds having a calixlike shape are described. Macrocyclic compounds were obtained vía self‐assembly reactions between salicylaldehyde carboxyl derivatives and 3‐aminophenylboronic acid, whereby the formation of three N–B coordination bonds favored the oligomerization process. The products are stable to moisture and have good solubility in organic solvents. The inclusion properties toward primary amines and pyrophosphate were analyzed by titration experiments and monitored by UV‐vis spectroscopy. Association constants around 103‐105 M−1 were determined for both compounds.

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“…[1][2][3][4][5][6][7][8][9] Azacalix [4]pyridines, for example, appear as powerful and selective hosts for metal ions, [10] neutral molecules, [11] while oxacalix [2]arene [2]triazines are able to form complexes with anions of various geometries and shapes through anion-π interactions. [12] Azacalix [4]pyrimidines act as divergent tectonic units to produce complexes with metals, [13] while the bowlshaped azacalix [3]pyridine [3]pyrimidines form complexes with fullerenes through multiple intermolecular π/π and CH/π interactions. [14] Till now a wide variety of heteracalixaromatics involving different combinations of pyridine, pyrimidine, pyrazine and triazine etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of Azacalix[2]pyrimidine[2]triazines and Their Self‐assembly in the Solid State

Wang

2014

Chin. J. Chem.

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A number of azacalix[2]pyrimidine[2]triazines were synthesized in moderate to good yields from both a step-wise fragment coupling approach and a one-pot reaction strategy starting from 4,6-diaminopyrimidines and cyanuric chloride. Nucleophilic aromatic substitution reaction of resulting dichloro-substituted azacalix[2]pyrimidine[2]triazines with NH 4 Cl led to the formation of NH 2 -bearing azacalix[2]pyrimidine[2]triazine analogs. Azacalix[2]pyrimidine[2]triazines adopted symmetric 1,3-alternate conformations in solution while twisted 1,3-alternate conformations were observed in the solid state. In the presence of different additives during the growth of single crystals, azacalix[2]pyrimidine[2]triazines containing amino (-NH 2 ) groups gave varied self-assembled structures due to the formation of different intermolecular hydrogen bond motifs.

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Azacalixarene: A New Class in the Calixarene Family

Cited by 133 publications

References 30 publications

Azacalix[6]arene Hexamethyl Ether: Synthesis, Structure, and Selective Uptake of Carbon Dioxide in the Solid State

Azacalix[6]arene Hexamethyl Ether: Synthesis, Structure, and Selective Uptake of Carbon Dioxide in the Solid State

Synthesis and inclusion properties of boroncalix[3]arene compounds obtained by self‐assembly of 3‐aminophenylboronic acid and salicylaldehyde derivatives

Synthesis and Structure of Azacalix[2]pyrimidine[2]triazines and Their Self‐assembly in the Solid State

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