Direct Detection of Hardly Detectable Hidden Chirality of Hydrocarbons and Deuterated Isotopomers by a Helical Polyacetylene through Chiral Amplification and Memory

Maeda, Katsuhiro; Hirose, Daisuke; Okoshi, Natsuki; Shimomura, Koichiro; Wada, Yuya; Ikai, Tomoyuki; Kanoh, Shigeyoshi; Yashima, Eiji

doi:10.1021/jacs.7b10981

Cited by 108 publications

(106 citation statements)

References 56 publications

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“…Chiral helical polymers have attracted much interest due to their intriguing helical structures and chiral amplification effect . They demonstrate substantial potential applications in chiral‐related fields including asymmetric catalysis, chiral recognition/separation, enantio‐selective release, enantio‐selective crystallization, etc.…”

Section: Methodsmentioning

confidence: 99%

A One‐Pot Polymerization for Concurrently Inducing Predominant Helicity in Optically Inactive Helical Polymer and Constructing Graphene‐Based Chiral Hybrid Foams

Song

et al. 2019

Macromol. Rapid Commun.

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Synthetic chiral helical polymers have achieved impressive progress in past few decades. Unfortunately, how to construct chiral helical polymer‐derived functional materials still remains highly challenging. The present contribution reports an unprecedented, one‐step strategy for judiciously combining chiral helical polymer with graphene to construct chiral hybrid foams. Graphene oxide (GO), ascorbic acid (L‐AA), Rh catalyst, and an achiral acetylenic monomer bearing phenylboronic acid group are mixed in an aqueous dispersion. Under mild conditions, the monomer underwent polymerization; meanwhile GO transforms into reduced graphene oxide (RGO) which in situ self‐assembles to construct a 3D porous structure. Herein, L‐AA simultaneously plays double roles: 1) working as a chiral source for the monomer to undergo helix‐sense‐selective polymerization or transferring its chirality to the polymer chains via forming borate structure; and 2) working as a reducing agent for reducing GO. The preparation strategy combines four processes into one single step: monomer polymerization, chirality transfer, reduction of GO, and RGO's self‐assembly. The eventually obtained chiral hybrid foams demonstrate advantages of porous structure, chirality, and reversible borate functional groups. The established preparation strategy promises a potent platform for conveniently constructing advanced chiral polymeric materials and even chiral hybrids starting from achiral monomers.

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Section: Methodsmentioning

confidence: 99%

A One‐Pot Polymerization for Concurrently Inducing Predominant Helicity in Optically Inactive Helical Polymer and Constructing Graphene‐Based Chiral Hybrid Foams

Song

et al. 2019

Macromol. Rapid Commun.

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“…[1][2][3] Changeable helicity is precedented by nature. [1][2][3] Changeable helicity is precedented by nature.…”

Section: Introductionmentioning

confidence: 99%

“…1 H NMR (300 MHz, DMSO-d 6 ) 12.6 (s, 1H), 8.0 (t, 1H, J = 5.8 Hz), 7.0 (t, 1H, J = 6.0 Hz), 3.8 (d, 2H, J = 5.8 Hz), 3.7 (d, 2H, J = 6.1 Hz), 1.4 (s, 9H). The scan rate was 600 nm/min, with a scan interval of 1.0 nm.…”

Section: Introductionmentioning

confidence: 99%

“…The UV-Vis absorption bands of supramolecular polymers R-1 (or S-1) (3 mL, 0.15 μmol, 0.05 mM in THF) were determined upon addition of Co(NO 3 ) 2 (0-1.0 equiv). 1 Synthesis of Compound S-1. Vibrational circular dichroism (VCD) spectra were obtained using a PRESTO-S-2016 VCD-LD spectrometer (JASCO Co. Ltd., Tokyo, Japan).…”

Section: Introductionmentioning

confidence: 99%

“…Vibrational Circular Dichroism Studies. 1 The VCD spectrophotometry was combined with linear dichroism.…”

Section: Introductionmentioning

confidence: 99%

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Helical Inversion of Peptide‐based Supramolecular Co²⁺ Complexes

Kim

Park

et al. 2018

Bulletin Korean Chem Soc

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Herein, we report the helical inversion of supramolecular polymeric complexes of Co 2+ containing a peptide-based ligand comprising one alanine and three glycine moieties and an achiral terpyridine group. The helicity of the peptide-based supramolecular polymer is controlled via strain-induced chirality at different stoichiometric ligand/Co 2+ ratios. The supramolecular polymer S-1 adopts octahedral geometry with right-handed helicity (P-type) in the presence of <0.7 equiv of Co 2+ . In contrast, it adopts coexisting octahedral and square-pyramidal geometries in the presence of 1.0 equiv of Co 2+ and presents left-handed helicity (M-type). The helicities of the supramolecular polymer R-1 with Co 2+ , prepared using the chirally opposite ligand, were completely opposite to those of S-1. Furthermore, the circular dichroism intensities of supramolecular polymers S-1 and R-1 in the presence of Co 2+ were 900-1500 times higher than those of free S-1 and R-1. In addition, the helical inversion was completely reversible and controllable by the addition of more Co 2+ or ligand.

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Supramolecular Chirality Transfer toward Chiral Aggregation: Asymmetric Hierarchical Self‐Assembly

2021

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Self-assembly, as a typical bottom-up strategy for the fabrication of functional materials, has been applied to fabricate chiral materials with subtle chiral nanostructures. The chiral nanostructures exhibit great potential in asymmetric catalysis, chiral sensing, chiral electronics, photonics, and even the realization of several biological functions. According to existing studies, the supramolecular chirality transfer process combined with hierarchical self-assembly plays a vital role in the fabrication of multiscale chiral structures. This progress report focuses on the hierarchical self-assembly of chiral or achiral molecules that aggregate with asymmetric spatial structures such as twisted bands, helices, and superhelices in different environments. Herein, recent studies on the chirality transfer induced self-assembly based on a variety of supramolecular interactions are summarized. In addition, the influence of different environments and the states of systems including solutions, condensed states, gel systems, interfaces on the asymmetric hierarchical self-assembly, and the expression of chirality are explored. Moreover, both the driving forces that facilitate chiral bias and the supramolecular interactions that play an important role in the expression, transfer, and amplification of the chiral sense are correspondingly discussed.

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Direct Detection of Hardly Detectable Hidden Chirality of Hydrocarbons and Deuterated Isotopomers by a Helical Polyacetylene through Chiral Amplification and Memory

Cited by 108 publications

References 56 publications

A One‐Pot Polymerization for Concurrently Inducing Predominant Helicity in Optically Inactive Helical Polymer and Constructing Graphene‐Based Chiral Hybrid Foams

A One‐Pot Polymerization for Concurrently Inducing Predominant Helicity in Optically Inactive Helical Polymer and Constructing Graphene‐Based Chiral Hybrid Foams

Helical Inversion of Peptide‐based Supramolecular Co²⁺ Complexes

Supramolecular Chirality Transfer toward Chiral Aggregation: Asymmetric Hierarchical Self‐Assembly

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Direct Detection of Hardly Detectable Hidden Chirality of Hydrocarbons and Deuterated Isotopomers by a Helical Polyacetylene through Chiral Amplification and Memory

Cited by 108 publications

References 56 publications

A One‐Pot Polymerization for Concurrently Inducing Predominant Helicity in Optically Inactive Helical Polymer and Constructing Graphene‐Based Chiral Hybrid Foams

A One‐Pot Polymerization for Concurrently Inducing Predominant Helicity in Optically Inactive Helical Polymer and Constructing Graphene‐Based Chiral Hybrid Foams

Helical Inversion of Peptide‐based Supramolecular Co2+ Complexes

Supramolecular Chirality Transfer toward Chiral Aggregation: Asymmetric Hierarchical Self‐Assembly

Contact Info

Product

Resources

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Helical Inversion of Peptide‐based Supramolecular Co²⁺ Complexes