Kinetically controlled Ag<sup>+</sup>-coordinated chiral supramolecular polymerization accompanying a helical inversion

Choi, Heekyoung; Heo, Seongkook; Lee, Seonae; Kim, Ka Young; Lim, Jong Hyeon; Jung, Sung Ho; Lee, Shim Sung; Lee, Jin Yong; Jung, Jong Hwa

doi:10.1039/c9sc04958d

Cited by 32 publications

(17 citation statements)

References 61 publications

(46 reference statements)

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“…The right-handed helicity of the free ligand based on bipyridine possessing the alanine moiety was converted to the left-handed helicity upon addition of Ag + by circular dichroism (CD) observation in our previous study. 6 However, AFM revealed one-handed helicity of the self-assemblies although the Ag + concentration revealed one handedness. 6 Thus, the presence of isolated right – and left-handed helical fibers induced by Ag + in one sample is a unique phenomenon, which indicates a new chiral self-sorting system that occurs due to free ligands and complexes with opposite helicities in a single enantiomeric component.…”

Section: Resultsmentioning

confidence: 99%

“… 6 However, AFM revealed one-handed helicity of the self-assemblies although the Ag + concentration revealed one handedness. 6 Thus, the presence of isolated right – and left-handed helical fibers induced by Ag + in one sample is a unique phenomenon, which indicates a new chiral self-sorting system that occurs due to free ligands and complexes with opposite helicities in a single enantiomeric component.…”

Section: Resultsmentioning

confidence: 99%

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Helicity-driven chiral self-sorting supramolecular polymerization with Ag⁺: right- and left-helical aggregates

Kim

Choi

et al. 2022

Chem. Sci.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Helicity-driven chiral self-sorting supramolecular polymerization with Ag⁺: right- and left-helical aggregates

Kim

Choi

et al. 2022

Chem. Sci.

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“…As this 3:2 complex featured a Ag + −Ag + interaction and a helical structure. 60,64,65 We expect that each Ag + ion was coordinated by three nitrogen atoms of three Bipy molecules (1G). The large upfield shift was ascribed to strong π−π stacking between Bipy moieties.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Dynamic Transformation of a Ag⁺-Coordinated Supramolecular Nanostructure from a 1D Needle to a 1D Helical Tube via a 2D Ribbon Accompanying the Conversion of Complex Structures

Kim

Park

et al. 2021

J. Am. Chem. Soc.

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We report a unique dynamic morphology transformation of a Ag +coordinated supramolecular nanostructure accompanying the conversion of complex structures in aqueous solution. In the presence of AgNO 3 (1.0 equiv), the achiral bipyridine-based ligand 1G, possessing hydrazine and glycine moieties, preferentially generated a 1D needle-like structure (nanostructure I) based on the 1GAgNO 3 complex (1G:Ag + = 1:1) as a metastable product. Nanostructure I was then transformed into nanostructure II, which was composed of the 1G 3 Ag 2 (NO 3 ) 2 complex (1G:Ag + = 3:2) as the thermodynamically stable product. This nanostructure exhibited a 1D helical tubular structure with a uniform diameter via a 2D ribbon as an intermediator, which led to the generation of a circular dichroism (CD) signal with right-handed (P-type) helicity. The observed dynamic transformation was attributed to formation of the thermodynamically favored helical 1G 3 Ag 2 (NO 3 ) 2 complex. In addition, the helical 1G 3 Ag 2 (NO 3 ) 2 complex acted as an initiator in the transformation from the 1D needle-like structure to the 1D helical tube via a 2D ribbon. The enhanced ΔG°value of nanostructure II compared to that of nanostructure I confirmed that nanostructure II is thermodynamically stable. More importantly, the transformation of supramolecular nanostructure I to nanostructure II occurred via an "on" pathway, even though the 1GAgNO 3 complex was converted to the 1G 3 Ag 2 (NO 3 ) 2 complex, which did not involve dissociation from nanostructure I into the monomeric 1GAgNO 3 complex species. In the kinetic study, the NO 3 − anion was found to act as an accelerator for the dynamic transformation from nanostructure I to nanostructure II. This result provides the first example of a dynamic transformation of a 1D needle-like structure into a 1D tubular structure via a 2D ribbon structure, accompanied by the conversion of a complex structure and the generation of a large CD signal for the metallosupramolecular nanostructure. This study may open up new avenues to the understanding of a dynamic morphology transformation process in biological systems.

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“…In addition to undergoing interesting morphological transitions, the DA-containing PDIs experience remarkable changes in absolute configurations at the supramolecular stereogenic centers during self-assembly 52,53 . This feature was probed by monitoring time-dependent circular dichroism (CD) spectra of 10% CHCl 3 / EtOH solutions (27 μM) of 1-R and 1-S (Fig.…”

Section: Resultsmentioning

confidence: 99%

Light-directed trapping of metastable intermediates in a self-assembly process

et al. 2020

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Self-assembly is a dynamic process that often takes place through a stepwise pathway involving formation of kinetically favored metastable intermediates prior to generation of a thermodynamically preferred supramolecular framework. Although trapping intermediates in these pathways can provide significant information about both their nature and the overall self-assembly process, it is a challenging venture without altering temperature, concentrations, chemical compositions and morphologies. Herein, we report a highly efficient and potentially general method for “trapping” metastable intermediates in self-assembly processes that is based on a photopolymerization strategy. By employing a chiral perylene-diimide possessing a diacetylene containing an alkyl chain, we demonstrated that the metastable intermediates, including nanoribbons, nanocoils and nanohelices, can be effectively trapped by using UV promoted polymerization before they form thermodynamic tubular structures. The strategy developed in this study should be applicable to naturally and synthetically abundant alkyl chain containing self-assembling systems.

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Kinetically controlled Ag⁺-coordinated chiral supramolecular polymerization accompanying a helical inversion

Abstract: The nanoparticles were transformed into the supramolecular polymer as the thermodynamic product, involving a helical inversion from left-handed to right-handed helicity.

Cited by 32 publications

References 61 publications

Helicity-driven chiral self-sorting supramolecular polymerization with Ag⁺: right- and left-helical aggregates

Helicity-driven chiral self-sorting supramolecular polymerization with Ag⁺: right- and left-helical aggregates

Dynamic Transformation of a Ag⁺-Coordinated Supramolecular Nanostructure from a 1D Needle to a 1D Helical Tube via a 2D Ribbon Accompanying the Conversion of Complex Structures

Light-directed trapping of metastable intermediates in a self-assembly process

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Kinetically controlled Ag+-coordinated chiral supramolecular polymerization accompanying a helical inversion

Abstract: The nanoparticles were transformed into the supramolecular polymer as the thermodynamic product, involving a helical inversion from left-handed to right-handed helicity.

Cited by 32 publications

References 61 publications

Helicity-driven chiral self-sorting supramolecular polymerization with Ag+: right- and left-helical aggregates

Helicity-driven chiral self-sorting supramolecular polymerization with Ag+: right- and left-helical aggregates

Dynamic Transformation of a Ag+-Coordinated Supramolecular Nanostructure from a 1D Needle to a 1D Helical Tube via a 2D Ribbon Accompanying the Conversion of Complex Structures

Light-directed trapping of metastable intermediates in a self-assembly process

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Product

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Kinetically controlled Ag⁺-coordinated chiral supramolecular polymerization accompanying a helical inversion

Helicity-driven chiral self-sorting supramolecular polymerization with Ag⁺: right- and left-helical aggregates

Helicity-driven chiral self-sorting supramolecular polymerization with Ag⁺: right- and left-helical aggregates

Dynamic Transformation of a Ag⁺-Coordinated Supramolecular Nanostructure from a 1D Needle to a 1D Helical Tube via a 2D Ribbon Accompanying the Conversion of Complex Structures