Synthesis and binding behavior of an artificial receptor based on “upper rim” functionalized calix[5]arene

Haino, Takeharu; Matsumura, Kazumi; Harano, Tetsuya; Yamada, Kazumasa; Saijyo, Y.; Fukazawa, Yoshimasa

doi:10.1016/s0040-4020(98)00750-9

Cited by 34 publications

(10 citation statements)

References 27 publications

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“…Suzuki coupling of a β-bromopyrrole with phenylboronic acid has been reported, but carbo(alko)xy-substituted boronic acids were not known to be participants in the Suzuki coupling reaction with pyrroles. The precursors, m -(methoxycarbonyl)phenyl boronic acid ( 12 m ) and its p -isomer ( 12 p ), were prepared inexpensively by a combination of literature methods. Commercially available m - or p -bromotoluene easily formed Grignard reagents, which were reacted (inverse addition at −78 °C) with trimethyl borate.…”

Section: Resultsmentioning

confidence: 99%

Novel Benzoic Acid Congeners of Bilirubin

Boiadjiev

Lightner

2003

J. Org. Chem.

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Three regioisomeric bilirubins and biliverdins with propionic acids replaced by benzoic acids were synthesized from the corresponding xanthobilirubic acids by oxidative coupling. The rubins were found to exhibit widely varying polarity, spectroscopic properties, and stereochemistry. The isomer with ortho benzoic acids (1 o ) was much less polar than either the meta (1 m ) or para (1 p ) because 1 o (but not 1 m and 1 p ) can adopt a folded conformation with both carboxylic acids intramolecularly hydrogen bonded to the opposing dipyrrinones. The consequences of such conformational differentiation are found in the varying 1H NMR, UV−vis, and circular dichroism spectral properties.

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Section: Resultsmentioning

confidence: 99%

Novel Benzoic Acid Congeners of Bilirubin

Boiadjiev

Lightner

2003

J. Org. Chem.

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“…Calix[5]arenes are macrocyclic molecules with a well-defined cavity owing to intramolecular cyclic hydrogen bonds among the five phenolic hydroxyl groups. − The large cavity fits the exterior of a [60]fullerene molecule to produce high selectivity in complexation as well as very strong binding affinity between these molecules, which allows easy access to fullerene-containing supramolecular architectures. − Thus, specific calixarene–fullerene binding should be suitable for the creation of shape-transformable polymers. Here, we report on the supramolecular approach for the specific shape transformation of [60]fullerene-terminated polymethyl methacrylate (PMMA) via calixarene–fullerene complexation (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Approach to Polymer-Shape Transformation via Calixarene–Fullerene Complexation

2020

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We synthesized fullerene-terminated polymethyl methacrylates (PMMAs), linear ditopic calix[5]arene host, and branched tritopic calix[5]arene host. The calix[5]arene hosts bound to the fullerene moieties of the PMMAs, inducing shape transformation among three different polymer shapes, namely, short PMMA, long PMMA, and star-shaped PMMA, in solution. The transformation was studied using UV/vis spectroscopy, fluorescence spectroscopy, diffusion ordered NMR spectroscopy, size-exclusion chromatography, viscometry, and differential scanning calorimetry. Dynamic light scattering measurements confirmed that the transformation between the individual shapes was induced by application of external stimuli, including prechosen molecules and heating of the solution. Of particular note is that atomic force microscopy revealed that PMMA illustrated an additional shape, namely, a spherical shape, in the solid state due to the cohesive nature of its fullerene moiety. The present study illustrated that a supramolecular approach to polymer-shape regulation allows access to multiple distinct polymer shapes in sequence.

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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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Synthesis and binding behavior of an artificial receptor based on “upper rim” functionalized calix[5]arene

Cited by 34 publications

References 27 publications

Novel Benzoic Acid Congeners of Bilirubin

Novel Benzoic Acid Congeners of Bilirubin

Supramolecular Approach to Polymer-Shape Transformation via Calixarene–Fullerene Complexation

Supramolecular Polymerization Engineered with Molecular Recognition

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