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

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

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 languageEnglish
Pages (from-to)2135-2141
Number of pages7
JournalJournal of the American Chemical Society
Volume145
Issue number4
DOIs
Publication statusPublished - 2023 Feb 1

Bibliographical note

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

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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