Chirality responsive helical poly(phenylacetylene) bearing <scp>L</scp>‐proline pendants

Kawamura, Hiroaki; Takeyama, Yoshihisa; Yamamoto, Miho; Kurihara, Hiroyuki; Morino, Kazuhide; Yashima, Eiji

doi:10.1002/chir.20954

Cited by 13 publications

(16 citation statements)

References 64 publications

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“…proline pendants, and show a unique helix-sense inversion in response to external, achiral and chiral stimuli (e.g., solvents and chiral small molecules). 41 For instance, 25 can enantioselectively capture 1,1 0 -2-binaphthol in its hydrophobic helical cavity inside the polymer in water and invert its helical sense in the presence of one of the enantiomers. PPAs having a b-cyclodextrin (CyD) moiety bonded to the phenyl ring through ester (26), ether, and amide linkages have been synthesized.…”

Section: Chirality-responsive Pasmentioning

confidence: 99%

Stimuli-Responsive Polyacetylenes and Dendronized Poly(phenylacetylene)s

Masuda

Zhang

2016

Polymer Reviews

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Combination of stimuli responsiveness with p-conjugated polymers possesses probabilities not only to provide these polymers with unique interesting properties but also to promote new functions including various optoelectronic properties, catalysis, ionic sensing, and chiral recognition. In the former part of this review, recent developments of stimuli-responsive polyacetylenes are surveyed, which act as receptors towards external stimuli such as solvent, temperature, pH, chiral compounds, metal cations, various anions, electricity, light, etc., to transduce to other signals or energies, which leads to a wide range of intriguing properties to mimic biological processes or applications to smart or intelligent materials. In the latter part, we introduce dendronized poly(phenylacetylene)s (PPAs) exhibiting interesting thermoresponsive and chiroptical properties. Thermoresponsiveness of these dendronized conjugated polymers shows synchronous influence on their helical and hydrated conformations.

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Section: Chirality-responsive Pasmentioning

confidence: 99%

Stimuli-Responsive Polyacetylenes and Dendronized Poly(phenylacetylene)s

Masuda

Zhang

2016

Polymer Reviews

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“…Atomic force microscopy, circular dichroism (CD) spectroscopy, and X‐ray crystallography were used to determine helical pitch and handedness of a polyphenylacetylenes carrying l ‐ and d ‐alanine with a long n ‐decyl chain . Inversion of helical sense in response to chiral stimuli of polyphenylacetylenes bearing l ‐proline pendants has also been reported …”

Section: Incorporation Of Amino Acids In the Side Chainmentioning

confidence: 99%

Side‐Chain Amino‐Acid‐Derived Cationic Chiral Polymers by Controlled Radical Polymerization

Bauri

Roy

2015

Macro Chemistry & Physics

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There is an increased interest in incorporation of naturally occurring amino acid/peptide moieties into the synthetic polymeric chain. Because of functional group diversity in amino acids, it is possible to synthesize a large variety of well-defi ned functional amino-acid/peptide-based optically active polymers with varied polymer length, composition, and architectures using available controlled/living polymerization techniques. The amino acid inclusion into the synthetic polymer chains may offer several advantages such as (a) functional group availability which not only results in improved hydrophilicity and possible interactions with proteins and genes but also facilitates further modifi cation with bioactive molecules, (b) introduces chirality, and (c) makes room for noncovalent interactions to form hierarchical superstructures. From the long past, amino acids have been extensively incorporated in the main chain of biodegradable polymers, and their biological importance have been evaluated. Besides, various sidechain amino-acid/peptide-bearing polymers have been synthesized and used for different purposes. In this article, utilization of different controlled/living polymerization methods to prepare various side-chain amino acid/peptide pendant polymers will be discussed, mainly focusing on cationic chiral polymeric architectures and 3D gel networks by reversible addition-fragmentation chain transfer polymerization.

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“…It is the only protein-forming amino acid with a secondary amino group. [19] Both proline-based molecular brushes [20] and dendronized polymers [11a,c] reported by our group demonstrate that a highly stable helical conformation can be achieved with proline moieties. [17] Owing to conformational restrictions imposed by the pyrrolidine ring, the proline moiety also plays an important role within peptides and proteins by acting as a turn inducer, although the amide linkage from the secondary amine cannot form strong hydrogen bonds.…”

Section: Introductionmentioning

confidence: 98%

Remarkable Structure Effects on Chiroptical Properties of Polyisocyanides Carrying Proline Pendants

et al. 2013

Chemistry An Asian Journal

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Chiral polymers with simple chemical structures and high helical conformation stabilities are important for their applications as chiral supports and asymmetrical catalysts. We report herein the synthesis of a series of aliphatic polyisocyanides carrying proline pendants of different chiralities, and an investigation of the effects of the chemical structures of these pendants on the chiroptical properties of the polymers. The configuration of the chiral center at the 4-position of the proline pendants was changed from S to R to check its effect on the handedness of the helical conformation. To examine the effects of steric hindrance on the stabilities of the helical conformation for these aliphatic representatives, proline pendants with various substituents at both the carboxyl and amine terminals were designed. To further examine the steric effects of the proline pendants, aromatic counterparts were also prepared. In the latter case, the effects of hydrogen bonds between pendant units on the enhancement and stabilities of the helical conformation were investigated by switching from the ester to an amide linkage. The Cotton effects and signal intensities of both aliphatic and aromatic polyisocyanides from circular dichroism spectroscopy were compared based on the bulkiness of the pendant groups, solvent polarities, and solution temperatures. It was found that highly stable helical conformations of polyisocyanides could be imposed by small bulky monoproline pendants.

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Chirality responsive helical poly(phenylacetylene) bearing L‐proline pendants

Cited by 13 publications

References 64 publications

Stimuli-Responsive Polyacetylenes and Dendronized Poly(phenylacetylene)s

Stimuli-Responsive Polyacetylenes and Dendronized Poly(phenylacetylene)s

Side‐Chain Amino‐Acid‐Derived Cationic Chiral Polymers by Controlled Radical Polymerization

Remarkable Structure Effects on Chiroptical Properties of Polyisocyanides Carrying Proline Pendants

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