5,20-Bis(ethoxycarbonyl)-Substituted Antiaromatic [28]Hexaphyrin and Its Bis-Ni II and Bis-Cu II Complexes

Akito Nakai, Jinseok Kim, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)


5,20-Bis(ethoxycarbonyl)-[28]hexaphyrin was synthesized by acid catalyzed cross-condensation of meso-diaryl-substituted tripyrrane and ethyl 2-oxoacetate followed by subsequent oxidation. This hexaphyrin was found to be a stable 28π-antiaromatic compound with a dumbbell-like conformation. Upon oxidization with PbO 2 , this [28]hexaphyrin was converted into an aromatic [26]hexaphyrin with a rectangular shape bearing two ester groups at the edge side. The [28]hexaphyrin can incorporate two Ni II or Cu II metals by using the ester carbonyl groups and three pyrrolic nitrogen atoms to give bis-Ni II and bis-Cu II complexes with essentially the same dumbbell-like structure. The antiaromatic properties of the [28]hexaphyrin and its metal complexes have been well characterized.

Original languageEnglish
Pages (from-to)968-971
Number of pages4
JournalChemistry - An Asian Journal
Issue number7
Publication statusPublished - 2019 Apr 1

Bibliographical note

Funding Information:
This work at Kyoto was supported by Grant-in-Aid from JSPS for Scientific Research (A): 18H03910, Challenging Exploratory Research: 18K19074. The work at Yonsei was supported by the Global Research Laboratory (GRL) Program funded by the Ministry of Science, ICT & Future, Korea (2013K1A1A2A02050183). The authors thank to Prof. Dr. Yorimitsu at Kyoto University for HR-MS measurements, and Prof. Dr. Maeda at Ritsumeikan University for MALDI TOF-MS measurements.

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry


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