Synthesis and chiroptical properties of a π-conjugated polymer containing glucose-linked biphenyl units in the main chain capable of folding into a helical conformation

Ikai, Tomoyuki; Shimizu, Syo; Awata, Seiya; Kudo, Tadashi; Yamada, Takayuki; Maeda, Katsuhiro; Kanoh, Shigeyoshi

doi:10.1039/c6py01759b

Cited by 27 publications

(27 citation statements)

References 52 publications

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“…Ikai's group polymerized thiophene with glucose-linked biphenyl units to afford a series of copolymers 36 with axial chirality. [59][60][61] All the copolymers exhibited CD and CPL signals in both solution and films indicating a helix structure of a single polymer chain. With the decrease of the thiophene rings, the structure irregularity due to the rotation of the C-C bond between thiophene rings reduced; as a result, less repeating units were needed to stabilize the helical structure of the polymer chain.…”

Section: Chirality Introduced By Substituents With Planar or Axial Chiralitymentioning

confidence: 96%

Chirality in polythiophenes: A review

Wang

Xiao

2021

Chirality

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Chiroptical polythiophene (PTh), as one of the most important chiral conductive polymers, is an emerging and hot topic in chiral materials, which shows great application potentials in fields as diverse as chiral sensing and separation, asymmetry catalysis, chiroptoelectronics, and even chirospintronics. This review summarizes progress in chiral polythiophenes (PThs) in the past 10 years, including the synthesis, properties and applications. Main focus is placed on the manner in which chirality is implemented and the optical activity of the chiral PThs. We showcase examples in which the chirality of PThs is induced by side chain substituents with point, planar, and axial chirality or arises from external chiral media. Application of chiral PThs is also included. Finally, perspectives for further development are offered.

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Section: Chirality Introduced By Substituents With Planar or Axial Chiralitymentioning

confidence: 96%

Chirality in polythiophenes: A review

Wang

Xiao

2021

Chirality

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“…Inspired by the sophisticated functions of biological helical polymers and their assemblies, a rich variety of artificial helical polymers has been prepared over the past decades in order to develop advanced chiral materials for the resolution of enantiomers by chromatography, sensing of chiral molecules, and circularly polarized luminescence . The application of optically active helical polymers for asymmetric catalysis has also attracted growing interest, because a one‐handed helical chirality can significantly contribute to the enantioselectivity due to a one‐handed helical arrangement of the catalytically active, chiral/achiral units along the one‐handed helical polymer backbone .…”

Section: Introductionmentioning

confidence: 99%

Helicity Induction and Its Static Memory of Poly(biphenylylacetylene)s Bearing Pyridine N‐Oxide Groups and Their Use as Asymmetric Organocatalysts

Ando

Ishidate

Ikai

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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Novel poly(biphenylylacetylene) derivatives carrying different types of pyridine N‐oxide units with a bulky or less‐bulky substituent at a different position as the functional pendant groups (poly‐2a and poly‐2b) were synthesized by the rhodium‐catalyzed polymerization of the corresponding monomers. The influence of the steric environment around the catalytically active pyridine N‐oxide sites on the helicity induction and its static memory as well as the asymmetric catalytic activities of the resulting helical polymers with a macromolecular helicity memory was investigated. The polyacetylenes formed an excess one‐handed helical conformation upon noncovalent interactions with optically active alcohols and the induced macromolecular helicities of the polyacetylenes were efficiently memorized after the removal of the chiral inducers. Poly‐2b with the macromolecular helicity memory showed an enantioselectivity for the catalytic asymmetric allylation of benzaldehydes, producing optically active allyl alcohols, although their enantioselectivities were low. On the other hand, poly‐2a exhibited a negligible catalytic activity probably due to the bulky substituent at the o‐position of the pyridine N‐oxide residues, while poly‐2a underwent a unique helix‐inversion with the increasing concentration of chiral alcohols and the opposite helicity of poly‐2a was further successfully memorized. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2481–2490

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“…Previously, the intensive excimer emission of 10 -5 M solutions of compound 1 in methylcyclohexane was reported [32]. Based on the earlier reports [34,35], we suggested that the polarity of a solvent can be the driving force for the geometry changes in the molecule of 1, which are highly soluble in non-polar solvents. In polar solvent media, this lipophilic molecule could act as a surfactant and the hydrophobic interactions would make molecule 1 to bend over the pentane linker.…”

Section: Resultsmentioning

confidence: 79%

“…Fig. 1 Synthetic scheme for sensor 1 However, in our experiments only a feeble response through the excimer fluorescence quenching with poor linearity in the Stern-Volmer plot was observed in cyclohexane.Based on the earlier reports[34,35], we suggested that the polarity of a solvent can be the driving force for the geometry changes in the molecule of 1, which are highly soluble in non-polar solvents. In polar solvent media, this lipophilic molecule could act as a surfactant and the hydrophobic interactions would make molecule 1 to bend over the pentane linker.…”

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confidence: 92%

Bispyrenylalkane Chemosensor for the Naked-eye Detection of Nitro-explosives

et al. 2021

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Pyrene-based compounds have a great potential as fluorescent chemosensors for various analytes including common nitro-explosives, such as 2,4,6-trinitrotoluene (TNT). Compounds having two pyrene units in one molecule, such as bispyrenylalkanes, are able to form stable, bright emissive in a visual wavelength region excimers both in non-polar and polar environments. In this work we wish to report that in non-polar solvents the excimer has poor chemosensing properties while in aqueous solutions it provides significant “turn-off” fluorescence response to TNT in the sub-nanomolar concentrations.

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Synthesis and chiroptical properties of a π-conjugated polymer containing glucose-linked biphenyl units in the main chain capable of folding into a helical conformation

Abstract: Naturally occurring ellagitannins provide us with inspiration for the development of a chiral π-conjugated polymer bearing glucose-linked biphenyl units in the main chain.

Cited by 27 publications

References 52 publications

Chirality in polythiophenes: A review

Chirality in polythiophenes: A review

Helicity Induction and Its Static Memory of Poly(biphenylylacetylene)s Bearing Pyridine N‐Oxide Groups and Their Use as Asymmetric Organocatalysts

Bispyrenylalkane Chemosensor for the Naked-eye Detection of Nitro-explosives

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