Helix Induction in Poly(phenylacetylene)s Bearing Achiral Oligoglycine Pendants by Chiral Oligopeptides in Water

Maeda, Katsuhiro; Tsukui, Hitoshi; Matsushita, Yasuyuki; Yashima, Eiji

doi:10.1021/ma071407s

Cited by 15 publications

(8 citation statements)

References 51 publications

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“…Chiral additives that interact with polymer chains through dynamic covalent bonds, 7 ionic interactions, 8 hydrogen bonding, 9 and host–guest interactions 10 have been used to shift the equilibrium between right- and left-handed helical conformations. Particular interest is currently focused on the utilization of weak nonbonding interactions such as dipole–dipole and dispersion interactions for the induction of single-handed screw-sense.…”

Section: Introductionmentioning

confidence: 99%

Protected amino acids as a nonbonding source of chirality in induction of single-handed screw-sense to helical macromolecular catalysts

et al. 2021

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Section: Introductionmentioning

confidence: 99%

Protected amino acids as a nonbonding source of chirality in induction of single-handed screw-sense to helical macromolecular catalysts

et al. 2021

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“…Specifically, we wanted to explore how conformational and configurational changes in the chiral residues placed closer to or further away from the main chain affect the helical sense of the polymer. Poly(phenylacetylene)s (PPAs) bearing amino acid or peptide residues as substituents generally adopt helical structures stabilized by hydrogen bonds between neighboring pendants (the n th and ( n +2) th residue or the nth and ( n +3) th residue), adopting a β‐sheet‐like orientation . In this case, the amide groups of the amino acid residues are antiperiplanar ( anti , ap ) to each other, which places the first chiral center closer to the polyene backbone, while the other chiral centers are placed further away.…”

Section: Introductionmentioning

confidence: 99%

Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers

et al. 2020

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The dynamic behavior of helical polymers bearing pendant groups with two chiral centers was studied. Controlled conformational changes at the chiral units placed either closer to or further away from the main chain promote different helical structures. Although the first residue is usually responsible for determining a specific helicity (P or M), we now found that the second chiral center is also able to induce a preferred helical sense when it is located closer in space to the main chain, thereby cancelling the order from the first chiral moiety. This result was achieved through proper coordination with a metal cation. As proof of concept, poly(phenylacetylene)s (PPAs) that bear one and two chiral amino acid units of different sizes and configuration combinations (l/d‐alanine and l/d‐phenylalanine) as pendants were evaluated. In total, ten polymers were studied. This constitutes the first report of axial control from a remote stereocenter in polymers bearing complex chiral pendants.

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“…In particular, the helical polymer capable of responding to a specific molecular recognition event has been recently become important based on the increasing demand to develop smart and intelligent polymer inspired by biological macromolecules 6–8. Through a number of sophisticated investigations, the molecular design of the binding sites has been found to be essential for the realization of the desired stimuli‐responsive helicity change 9–38. Thus, the novel and unprecedented molecular design of the interaction site has the significant potential to expand the limit and scope in the field of stimuli‐responsive helical polymers.…”

Section: Introductionmentioning

confidence: 99%

Host–guest complexation‐triggered chiroptical change of poly(phenylacetylene)s bearing binaphthocrown ether moieties on the main chain

Sakai

Yonekawa

Otsuka

et al. 2010

J. Polym. Sci. A Polym. Chem.

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Diacetylene monomers with respective lengths of the oxyethylene chains were cyclopolymerized with a rhodium catalyst to produce novel poly(phenylacetylene)s bearing a different cavity size of the chiral crown ether in the repeating units (2a-c). In the circular dichroism spectra of the resulting polymers, characteristic Cotton effects were observed in the range from 350 to 500 nm corresponding to the absorption of the conjugated polymer backbone, indicating that the polymers possessed a helical structure with an excess single screw sense induced by the covalently bonded binaphthyl units. The host-guest complexation of 2a-c with achiral guests produced a chiroptical change based on the fluctuation in the main chain conformation. The behavior of the complexation-induced chiroptical change was essentially dictated by the cavity size of the binaphthocrown ether units. Additionally, a chiralityresponsive helicity change was observed in the case of the complexation of 2a-c with chiral guests, which also depended on the crown ether size.

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Helix Induction in Poly(phenylacetylene)s Bearing Achiral Oligoglycine Pendants by Chiral Oligopeptides in Water

Cited by 15 publications

References 51 publications

Protected amino acids as a nonbonding source of chirality in induction of single-handed screw-sense to helical macromolecular catalysts

Protected amino acids as a nonbonding source of chirality in induction of single-handed screw-sense to helical macromolecular catalysts

Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers

Host–guest complexation‐triggered chiroptical change of poly(phenylacetylene)s bearing binaphthocrown ether moieties on the main chain

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