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Realization of Stacked-Ring Aromaticity in a Water-Soluble Micellar Capsule
[Image: see text] 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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9896547/ https://www.ncbi.nlm.nih.gov/pubmed/36210512 http://dx.doi.org/10.1021/jacs.2c08795 |
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author | Liu, Si-Yu Kishida, Natsuki Kim, Jinseok Fukui, Norihito Haruki, Rie Niwa, Yasuhiro Kumai, Reiji Kim, Dongho Yoshizawa, Michito Shinokubo, Hiroshi |
author_facet | Liu, Si-Yu Kishida, Natsuki Kim, Jinseok Fukui, Norihito Haruki, Rie Niwa, Yasuhiro Kumai, Reiji Kim, Dongho Yoshizawa, Michito Shinokubo, Hiroshi |
author_sort | Liu, Si-Yu |
collection | PubMed |
description | [Image: see text] 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. |
format | Online Article Text |
id | pubmed-9896547 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-98965472023-02-04 Realization of Stacked-Ring Aromaticity in a Water-Soluble Micellar Capsule Liu, Si-Yu Kishida, Natsuki Kim, Jinseok Fukui, Norihito Haruki, Rie Niwa, Yasuhiro Kumai, Reiji Kim, Dongho Yoshizawa, Michito Shinokubo, Hiroshi J Am Chem Soc [Image: see text] 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. American Chemical Society 2022-10-10 /pmc/articles/PMC9896547/ /pubmed/36210512 http://dx.doi.org/10.1021/jacs.2c08795 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/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/). |
spellingShingle | Liu, Si-Yu Kishida, Natsuki Kim, Jinseok Fukui, Norihito Haruki, Rie Niwa, Yasuhiro Kumai, Reiji Kim, Dongho Yoshizawa, Michito Shinokubo, Hiroshi Realization of Stacked-Ring Aromaticity in a Water-Soluble Micellar Capsule |
title | Realization of Stacked-Ring
Aromaticity in a Water-Soluble
Micellar Capsule |
title_full | Realization of Stacked-Ring
Aromaticity in a Water-Soluble
Micellar Capsule |
title_fullStr | Realization of Stacked-Ring
Aromaticity in a Water-Soluble
Micellar Capsule |
title_full_unstemmed | Realization of Stacked-Ring
Aromaticity in a Water-Soluble
Micellar Capsule |
title_short | Realization of Stacked-Ring
Aromaticity in a Water-Soluble
Micellar Capsule |
title_sort | realization of stacked-ring
aromaticity in a water-soluble
micellar capsule |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9896547/ https://www.ncbi.nlm.nih.gov/pubmed/36210512 http://dx.doi.org/10.1021/jacs.2c08795 |
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