Metal-induced supramolecular chirality inversion of small self-assembled molecules in solution

Kokan, Zoran; Perić, Berislav; Vazdar, Mario; Marinić, Željko; Vikić‐Topić, Dražen; Meštrović, Ernest; Kirin, Srećko I.

doi:10.1039/c6cc09203a

Cited by 32 publications

(30 citation statements)

References 63 publications

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“…The proximity of cyclohexane rings is evidenced by the distance of 4.672 Å between farthest carbon atoms what is comparable to the distance found in the crystal structure of a 1,3,5‐cyclohexanetriamide,[9e] where the stacked cyclohexane rings also exhibit M ‐helical chirality.…”

Section: Resultssupporting

confidence: 70%

“…J ( 195 Pt, 31 P) ≈ 3650 Hz were assigned as cis ‐ square planar isomer. [9c] The singlet line for the trans ‐isomer was found at about δ ≈ 20.5 ppm, the satellite doublet originating from the J ( 195 Pt, 31 P) coupling was too weak to be obtained.…”

Section: Resultsmentioning

confidence: 99%

“…In the literature, ferrocene‐based selective catalysts A are well known and in part commercially available . In addition, ferrocene‐based amino acid derivatives B are extensively described and well understood, featuring only a very small number of chiral secondary structures with inter‐strand hydrogen bonding, where L ‐amino acids specifically induce P ‐helical chirality of the metallocene moiety , . If the selective ferrocene catalysts A and ferrocene amino acids B are combined, the structure C is obtained.…”

Section: Introductionmentioning

confidence: 99%

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“Backdoor Induction” of Chirality: Trans‐1,2‐cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts

et al. 2018

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This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine‐tuning the steric and/or electronic properties. Cis square‐planar metal complexes of RhI and PtII with ML2 stoichiometry have been prepared and characterized by spectroscopic methods (NMR, IR, UV‐Vis, CD) and DFT calculations. A key feature of the metal complexes is a prochiral metal coordination sphere and “backdoor induction” of chirality from a distant chiral source via an outer‐coordination sphere, well‐defined by aromatic stacking and hydrogen‐bonding. The rhodium complexes were used as catalysts in asymmetric hydrogenation of α,β‐dehydroamino acids with excellent yield and selectivity (up to 97 % ee), strongly supporting the “backdoor induction” hypothesis.

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Section: Resultssupporting

confidence: 70%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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“Backdoor Induction” of Chirality: Trans‐1,2‐cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts

et al. 2018

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“…In addition, the coordination of metal ions with chiral molecules was also applied as as trategy to adjust supramolecular chirality. [28] Kirin et al [29] reported that ah ydrogen-bonded chiral aminopyridine ligand exhibited supramolecular chirality in solution, independent of the organic solvent used. However, the supramolecular chirality was completely inverted by complexation to zinc ions.…”

Section: Dynamic Modulation At the Intramolecular Levelmentioning

confidence: 99%

“…Mode transformation of acylaminopyridine molecules by additive zinc ions, resulting in the reversal of supramolecular chirality.R eproduced with permission from Ref [29][40]…”

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confidence: 99%

Dynamic Modulation of Supramolecular Chirality Driven by Factors from Internal to External Levels

Yue

Zhu

2019

Chemistry An Asian Journal

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Supramolecular chirality, generated by the asymmetric assembly of chiral or achiral molecules, has attracted intense study owing to its potential to offer insights into natural biological structures and its crucial roles in advanced materials. The optical activity and stacking pathway of building molecules both greatly determine the chirality of the whole supramolecular structure. The flexibility of supramolecular structures makes their chirality easy to modulate through abundant means. Adjustment of the molecular structure or packing mode, or external stimuli that act like a finger gently pushing toy bricks, can greatly change the chirality of supramolecular assemblies. The dynamic regulation of chiral nanostructures on the intramolecular, intermolecular, and external levels could be regarded as the modulatory essence in numerous strategies, however, this perspective is ignored in most reviews in the literature. Herein, therefore, we focus on the ingenious dynamic modulation of chiral nanostructures by these factors. Through dynamic modulation with changes in chiroptical spectroscopy and electron microscopy, the mechanism of formation of supramolecular chirality is also elaborated.

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Metal‐Ion‐Mediated Supramolecular Chirality of l‐Phenylalanine Based Hydrogels

Wang

Feng

2018

Angewandte Chemie

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Forchiral hydrogels and related applications,one of the critical issues is howtocontrol the chirality of supramolecular systems in an efficient way, including easy operation, efficient transfer of chirality,a nd so on. Herein, supramolecular chirality of l-phenylalanine based hydrogels can be effectively controlled by using abroad range of metal ions.The degree of twisting (twist pitch) and the diameter of the chiral nanostructures can also be efficiently regulated. These are ascribed to the synergic effect of hydrogen bonding and metal ion coordination. This study may develop am ethod to design an ew class of electronically,o ptically,a nd biologically active materials.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Metal-induced supramolecular chirality inversion of small self-assembled molecules in solution

Cited by 32 publications

References 63 publications

“Backdoor Induction” of Chirality: Trans‐1,2‐cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts

“Backdoor Induction” of Chirality: Trans‐1,2‐cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts

Dynamic Modulation of Supramolecular Chirality Driven by Factors from Internal to External Levels

Metal‐Ion‐Mediated Supramolecular Chirality of l‐Phenylalanine Based Hydrogels

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