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 journalArticle

1 Citation (Scopus)

Abstract

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
Volume14
Issue number7
DOIs
Publication statusPublished - 2019 Apr 1

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Esters
Bearings (structural)
Coordination Complexes
Conformations
Condensation
Nitrogen
Metals
Atoms
Oxidation
Acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

Cite this

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abstract = "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.",
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5,20-Bis(ethoxycarbonyl)-Substituted Antiaromatic [28]Hexaphyrin and Its Bis-Ni II and Bis-Cu II Complexes . / Nakai, Akito; Kim, Jinseok; Kim, Dongho; Osuka, Atsuhiro.

In: Chemistry - An Asian Journal, Vol. 14, No. 7, 01.04.2019, p. 968-971.

Research output: Contribution to journalArticle

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AB - 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.

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