Preparation and characterization of novel optically active polyurethanes containing 1,1′‐binaphthol

Chen, Jing; Nan, Qiuli; Le, Guo; Zhou, Yuming

doi:10.1002/app.31355

Cited by 5 publications

(4 citation statements)

References 19 publications

(12 reference statements)

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“…Biaryl compounds are classic atropisomers and are liable to form stable enantiomers due to their shorter C (sp 2 )-C (sp 2 ) bond length (1.49 Å) than C (sp 3 )-C (sp 3 ) bond length (1.52 Å). 18,19 When there are substituents at the ortho-position of the biaryl axis, such as binaphthol 20 and bifendatatum, 21 the rotational In recent years, many natural products with biaryl moieties have been reported. Mbandakamines, possessing anti-Plasmodium activity, are dimers of naphthylisoquinoline alkaloids isolated from the leaves of a Congolese Ancistrocladus species.…”

Section: Classic Atropisomersmentioning

confidence: 99%

“…Biaryl compounds are classic atropisomers and are liable to form stable enantiomers due to their shorter C (sp 2 )‐C (sp 2 ) bond length (1.49 Å) than C (sp 3 )‐C (sp 3 ) bond length (1.52 Å) 18,19 . When there are substituents at the ortho ‐position of the biaryl axis, such as binaphthol 20 and bifendatatum, 21 the rotational energy barrier is large enough to form Class 3 atropisomers.…”

Section: Classification Of Atropisomersmentioning

confidence: 99%

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A nonneglectable stereochemical factor in drug development: Atropisomerism

Yang

2022

Chirality

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Chirality is one of the key factors affecting the medicinal efficacy of compounds. In addition to central chirality, sterically hindered chiral axes commonly appear in drugs and the resulting chirality is known as atropisomerism. With developments in medicinal chemistry, atropisomerism has attracted increasing attention. This review discusses the classification, biological activity, pharmacokinetics, toxicity and side effects of atropisomers, and can serve as a reference in the research and development of potential chiral drugs.

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Section: Classic Atropisomersmentioning

confidence: 99%

Section: Classification Of Atropisomersmentioning

confidence: 99%

A nonneglectable stereochemical factor in drug development: Atropisomerism

Yang

2022

Chirality

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“…The ultrasonic method is a simple and inexpensive route to synthesize the polymer/nanoparticles, which can be extended to prepare a novel low infrared emissivity material. Zhou's group [234] also described the synthesis and the properties of novel optically active PUs based on chiral binaphthol via direct step-growth polymerization. The effect of optical purity on the specific rotation of the polymers was studied and results showed that the specific rotation of the polymer kept increasing with the optical purity, it may be explained that the increment of the optical purity caused a bigger chiral groups density.…”

Section: Polyurethanesmentioning

confidence: 99%

Advances in synthetic optically active condensation polymers - A review

Mallakpour

Zadehnazari²,

Iran³

2011

Express Polym. Lett.

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Abstract. The study of optically active polymers is a very active research field, and these materials have exhibited a number of interesting properties. Much of the attention in chiral polymers results from the potential of these materials for several specialized utilizations that are chiral matrices for asymmetric synthesis, chiral stationary phases for the separation of racemic mixtures, synthetic molecular receptors and chiral liquid crystals for ferroelectric and nonlinear optical applications. Recently, highly efficient methodologies and catalysts have been developed to synthesize various kinds of optically active compounds. Some of them can be applied to chiral polymer synthesis. In a few synthetic approaches for optically active polymers, chiral monomer polymerization has essential advantages in applicability of monomer, apart from both asymmetric polymerization of achiral or prochiral monomers and enantioselective polymerization of a racemic monomer mixture. The following are the up to date successful approaches to the chiral synthetic polymers by condensation polymerization reaction of chiral monomers.

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“…TGA showed that the resulting polymer was stable up to 392 °C before it started to lose mass . Chen et al have synthesized optically active polyurethanes containing 1,1'‐binaphthol by direct hydrogen transfer addition polymerization and found that the chiral polyurethanes had better thermal stablility …”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a chiral copoly(ether sulfone) with high molecular weight

Zhang

Wang

et al. 2013

Polym. Int.

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A series of chiral poly(ether sulfone)s containing (S)-binaphthyl unit were synthesized via nucleophilic substitution polycondensation. The as-synthesized polymers were characterized by NMR. The molecular weights of these polymers were calculated by viscosity and gel permeation chromatography. The thermal stability was measured by TGA. The optical activities of the polymers were studied by circular dichroism and optical rotation. It was found that introducing more reactive 2,2 -biphenol monomer to partly substitute the binaphthol monomer could increase the molecular weight of the polymer from 4.1 × 10 4 to 9.8 × 10 4 g mol −1 . Meanwhile, the thermal stability increased and the decomposition temperature rose from 447 to 518 • C, with the optical activity of the polymer well preserved. However, the value of the specific optical rotation decreased with increasing biphenol to binaphthol molar ratio. In addition, the optical rotation direction of the polymer was contrary to that of the pristine binaphthol monomer, which indicated that the chiral polymers formed a secondary structure.

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Preparation and characterization of novel optically active polyurethanes containing 1,1′‐binaphthol

Cited by 5 publications

References 19 publications

A nonneglectable stereochemical factor in drug development: Atropisomerism

A nonneglectable stereochemical factor in drug development: Atropisomerism

Advances in synthetic optically active condensation polymers - A review

Synthesis and characterization of a chiral copoly(ether sulfone) with high molecular weight

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