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

Si Yu Liu; Natsuki Kishida; Jinseok Kim; Norihito Fukui; Rie Haruki; Yasuhiro Niwa; Reiji Kumai; Dongho Kim; Michito Yoshizawa; Hiroshi Shinokubo

doi:10.1021/jacs.2c08795

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

Si Yu Liu, Natsuki Kishida, Jinseok Kim, Norihito Fukui, Rie Haruki, Yasuhiro Niwa, Reiji Kumai, Dongho Kim, Michito Yoshizawa, Hiroshi Shinokubo

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	2135-2141
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	145
Issue number	4
DOIs	https://doi.org/10.1021/jacs.2c08795
Publication status	Published - 2023 Feb 1

Bibliographical note

Funding Information:
This work was supported by JSPS KAKENHI grants JP20H05862, JP20H05863, JP22H04974, and JP20H05867. This work was also supported by the JSPS A3 Foresight Program. S.-Y.L. expresses her gratitude for a JSPS Research Fellowship for Young Scientists (JP21J14071) and the “Graduate Program of Transformative Chem-Bio Research” at Nagoya University, supported by MEXT (WISE Program). XAFS measurements were conducted at the BL12C beam line at the Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization (KEK), under the approval of the Photon Factory Advisory Committee (no. 2022P005). H.S. gratefully acknowledges the Ogasawara Foundation for the Promotion of Science and Engineering for financial support.

Publisher Copyright:
© 2022 The Authors. Published by American Chemical Society.

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.2c08795

Cite this

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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.",

author = "Liu, {Si Yu} and Natsuki Kishida and Jinseok Kim and Norihito Fukui and Rie Haruki and Yasuhiro Niwa and Reiji Kumai and Dongho Kim and Michito Yoshizawa and Hiroshi Shinokubo",

note = "Funding Information: This work was supported by JSPS KAKENHI grants JP20H05862, JP20H05863, JP22H04974, and JP20H05867. This work was also supported by the JSPS A3 Foresight Program. S.-Y.L. expresses her gratitude for a JSPS Research Fellowship for Young Scientists (JP21J14071) and the “Graduate Program of Transformative Chem-Bio Research” at Nagoya University, supported by MEXT (WISE Program). XAFS measurements were conducted at the BL12C beam line at the Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization (KEK), under the approval of the Photon Factory Advisory Committee (no. 2022P005). H.S. gratefully acknowledges the Ogasawara Foundation for the Promotion of Science and Engineering for financial support. Publisher Copyright: {\textcopyright} 2022 The Authors. Published by American Chemical Society.",

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

Abstract

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