Realization of Stacked-Ring Aromaticity in a Water-Soluble Micellar Capsule

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Abstract

Stacked-ring aromaticity arising from the close stacking of antiaromatic π-systems has recently received considerable attention. Here, we realize stacked-ring aromaticity via a rational supramolecular approach. A nanocapsule composed of bent polyaromatic amphiphiles was employed to encapsulate several antiaromatic norcorrole Ni(II) complexes (NCs) in water. The resulting micellar capsules display high stability toward heating and concentration change. The encapsulation resulted in the appearance of a broad absorption band in the near-infrared region, which is characteristic of norcorroles with close face-to-face stacking. Importantly, a meso-isopropyl NC, which does not exhibit π-stacking even in a concentrated solution or the crystalline phase, adopted π-stacking with stacked-ring aromaticity in the supramolecular micellar capsule.

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Living supramolecular polymerization realized through a biomimetic approach.

Soichiro Ogi, Kazunori Sugiyasu, Swarup Manna … (2014)

Various conventional reactions in polymer chemistry have been translated to the supramolecular domain, yet it has remained challenging to devise living supramolecular polymerization. To achieve this, self-organization occurring far from thermodynamic equilibrium--ubiquitously observed in nature--must take place. Prion infection is one example that can be observed in biological systems. Here, we present an 'artificial infection' process in which porphyrin-based monomers assemble into nanoparticles, and are then converted into nanofibres in the presence of an aliquot of the nanofibre, which acts as a 'pathogen'. We have investigated the assembly phenomenon using isodesmic and cooperative models and found that it occurs through a delicate interplay of these two aggregation pathways. Using this understanding of the mechanism taking place, we have designed a living supramolecular polymerization of the porphyrin-based monomers. Despite the fact that the polymerization is non-covalent, the reaction kinetics are analogous to that of conventional chain growth polymerization, and the supramolecular polymers were synthesized with controlled length and narrow polydispersity.

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Chemical reactivity under nanoconfinement

Angela Grommet, Moran Feller, Rafal Klajn (2020)

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Design and Applications of Water-Soluble Coordination Cages

Edmundo Percástegui, Tanya K Ronson, Jonathan R. Nitschke (2020)

Compartmentalization of the aqueous space within a cell is necessary for life. In similar fashion to the nanometer-scale compartments in living systems, synthetic water-soluble coordination cages (WSCCs) can isolate guest molecules and host chemical transformations. Such cages thus show promise in biological, medical, environmental, and industrial domains. This review highlights examples of three-dimensional synthetic WSCCs, offering perspectives so as to enhance their design and applications. Strategies are presented that address key challenges for the preparation of coordination cages that are soluble and stable in water. The peculiarities of guest binding in aqueous media are examined, highlighting amplified binding in water, changing guest properties, and the recognition of specific molecular targets. The properties of WSCC hosts associated with biomedical applications, and their use as vessels to carry out chemical reactions in water, are also presented. These examples sketch a blueprint for the preparation of new metal–organic containers for use in aqueous solution, as well as guidelines for the engineering of new applications in water.

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Author and article information

Journal

Journal ID (nlm-ta): J Am Chem Soc

Journal ID (iso-abbrev): J Am Chem Soc

Journal ID (publisher-id): ja

Journal ID (coden): jacsat

Title: Journal of the American Chemical Society

Publisher: American Chemical Society

ISSN (Print): 0002-7863

ISSN (Electronic): 1520-5126

Publication date (Electronic): 10 October 2022

Publication date Collection: 01 February 2023

Volume: 145

Issue: 4

Pages: 2135-2141

Affiliations

[† ]Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, and Integrated Research Consortium on Chemical Sciences (IRCCS), Nagoya University , Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan

[‡ ]Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology , 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan

[§ ]Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University , Seoul 03722, Korea

[∥ ]PRESTO, Japan Science and Technology Agency (JST) , Kawaguchi, Saitama 332-0012, Japan

[⊥ ]Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization (KEK) , Tsukuba 305-0801, Japan

Author notes

[* ]Email: dongho@ 123456yonsei.ac.kr .

[* ]Email: yoshizawa.m.ac@ 123456m.titech.ac.jp .

[* ]Email: hshino@ 123456chembio.nagoya-u.ac.jp .

Author information

Norihito Fukui https://orcid.org/0000-0002-0466-0116

Yasuhiro Niwa https://orcid.org/0000-0001-5808-5594

Dongho Kim https://orcid.org/0000-0001-8668-2644

Michito Yoshizawa https://orcid.org/0000-0002-0543-3943

Hiroshi Shinokubo https://orcid.org/0000-0002-5321-2205

Article

DOI: 10.1021/jacs.2c08795

PMC ID: 9896547

PubMed ID: 36210512

SO-VID: d8512445-e8ed-47fa-a37b-72e0747f9707

License:

Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).