Synthesis of a new receptor based on “Upper Rim” functionalized calix[5]arene

Haino, Takeharu; Harano, Tetsuya; Matsumura, Kazumi; Fukazawa, Yoshimasa

doi:10.1016/0040-4039(95)01130-a

Cited by 24 publications

(15 citation statements)

References 23 publications

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“…A myriad of reports on how to substitute the calixarene moiety with various aromatic systems is found in the literature. [15][16][17][18][19][20][21][22] Earlier studies 23 on 5,17-disubstituted calix [4]arenes have shown that the substituent is generally pointing away from the cavity or when the conformation is dependent upon the solvent conditions the substituents associate, in both cases making interaction with a guest molecule difficult.…”

Section: Introductionmentioning

confidence: 99%

“…This problem can be solved by attaching substituents to the calixarene system so as to increase the apparent size of the cavity in the host molecule, thus making room for a larger guest molecule. A myriad of reports on how to substitute the calixarene moiety with various aromatic systems is found in the literature. − Earlier studies on 5,17-disubstituted calix[4]arenes have shown that the substituent is generally pointing away from the cavity or when the conformation is dependent upon the solvent conditions the substituents associate, in both cases making interaction with a guest molecule difficult.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Structural Properties of 5,17-Bis(N-methyl-N-arylaminocarbonyl)calix[4]arenes. Directing the Substituents toward the Cavity by Use of the Cis-Generating Property of theN-Methylaminocarbonyl Linker

et al. 1998

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A series of cone 5,17-bis(N-arylaminocarbonyl)calix [4]arenes were synthesized and N-methylated using an easy and high-yielding methylation procedure. The structures of the cone 5,17-bis(Nmethyl-N-arylaminocarbonyl)calix[4]arenes were studied in solution by NMR spectroscopy and in the solid state by X-ray structural resolution. The use of the N-methylaminocarbonyl linker between the calix[4]arene and the aromatic substituent was found to have a dominant influence on the molecular structure, forcing the substituent toward the cavity of the calix[4]arene regardless of the size of the substituent. The linker may be a very useful structure generator when considering the design of molecular receptors.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Properties of 5,17-Bis(N-methyl-N-arylaminocarbonyl)calix[4]arenes. Directing the Substituents toward the Cavity by Use of the Cis-Generating Property of theN-Methylaminocarbonyl Linker

et al. 1998

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“…The introduction of functionalities on the upper rim of calix[5]arene revealed its bright future as a host molecule. Our studies disclosed the remarkable abilities of molecular recognitions on calix[5]arene as well as calix[4]arene …”

Section: Development Of Supramolecular Fullerene Polymersmentioning

confidence: 87%

Supramolecular Polymerization Engineered with Molecular Recognition

Haino

2015

The Chemical Record

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Supramolecular polymeric assemblies represent an emerging, promising class of molecular assemblies with enormous versatility compared with their covalent polymeric counterparts. Although a large number of host-guest motifs have been produced over the history of supramolecular chemistry, only a limited number of recognition motifs have been utilized as supramolecular connections in polymeric assemblies. This account describes the molecular recognition of host molecules based on calix[5]arene and bisporphyrin that demonstrate unique guest encapsulations; subsequently, these host-guest motifs are applied to the synthesis of supramolecular polymers that display polymer-like properties in solution and solid states. In addition, new bisresorcinarenes are developed to form supramolecular polymers that are connected via a rim-to-rim hydrogen-bonded dimeric structure, which is composed of two resorcinarene moieties.

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“…A calix [5]arene was considered to be a potential candidate. [84][85][86][87] In fact, a large molecular guest, [60]fullerene, was encapsulated in the cone cavity. 88,89 In addition, the covalent connection of two calix [5]arene molecules generated a larger cavity capable of encapsulating [60]fullerene, as well as higher fullerenes, which resulted in a large increase in the association constants (Ka410 4-5 l mol -1 ).…”

Section: Supramolecular Fullerene Polymermentioning

confidence: 99%

Molecular-recognition-directed formation of supramolecular polymers

Haino

2012

Polym J

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In recent years, significant research effort has focused on creating supramolecular polymers that can be attained by specific host-guest interactions of the repeating units. During the supramolecular polymerization process, molecular recognition events, which are predetermined by the molecular building blocks, are highly selective and directional for defining the size, direction and dimension of the resulting supramolecular polymers. The diversity of the supramolecular building blocks ranges from small aromatic units to macrocycles. Recently, the interplay of supramolecular and polymer chemistry has led to the creation of novel supramolecular materials, which display fascinating functions such as self-healing, stimuli-responsiveness and rubber-like elastomeric properties. Supramolecular cross-linking and supramolecular block copolymerization are the methods that have been used to install fascinating and functional moieties onto polymer backbones. Currently, the development of practical supramolecular polymeric materials is an ongoing challenge for supramolecular chemists. This review will focus on the recent developments in supramolecular polymers composed of discrete repeating units, as well as novel supramolecular materials produced by the interplay of supramolecular and polymer chemistry.

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Synthesis of a new receptor based on “Upper Rim” functionalized calix[5]arene

Cited by 24 publications

References 23 publications

Synthesis and Structural Properties of 5,17-Bis(N-methyl-N-arylaminocarbonyl)calix[4]arenes. Directing the Substituents toward the Cavity by Use of the Cis-Generating Property of theN-Methylaminocarbonyl Linker

Synthesis and Structural Properties of 5,17-Bis(N-methyl-N-arylaminocarbonyl)calix[4]arenes. Directing the Substituents toward the Cavity by Use of the Cis-Generating Property of theN-Methylaminocarbonyl Linker

Supramolecular Polymerization Engineered with Molecular Recognition

Molecular-recognition-directed formation of supramolecular polymers

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