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

doi:10.1002/asia.201900189

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

Department of Chemistry

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

7 Citations (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 language	English
Pages (from-to)	968-971
Number of pages	4
Journal	Chemistry - An Asian Journal
Volume	14
Issue number	7
DOIs	https://doi.org/10.1002/asia.201900189
Publication status	Published - 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

Access to Document

10.1002/asia.201900189

Cite this

Nakai, A., Kim, J., Kim, D., & Osuka, A. (2019). 5,20-Bis(ethoxycarbonyl)-Substituted Antiaromatic [28]Hexaphyrin and Its Bis-Ni ^II and Bis-Cu ^II Complexes Chemistry - An Asian Journal, 14(7), 968-971. https://doi.org/10.1002/asia.201900189

Nakai, Akito ; Kim, Jinseok ; Kim, Dongho et al. / 5,20-Bis(ethoxycarbonyl)-Substituted Antiaromatic [28]Hexaphyrin and Its Bis-Ni ^II and Bis-Cu ^II Complexes In: Chemistry - An Asian Journal. 2019 ; Vol. 14, No. 7. pp. 968-971.

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

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.",

author = "Akito Nakai and Jinseok Kim and Dongho Kim and Atsuhiro Osuka",

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: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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Nakai, A, Kim, J, Kim, D & Osuka, A 2019, ' 5,20-Bis(ethoxycarbonyl)-Substituted Antiaromatic [28]Hexaphyrin and Its Bis-Ni ^II and Bis-Cu ^II Complexes ', Chemistry - An Asian Journal, vol. 14, no. 7, pp. 968-971. https://doi.org/10.1002/asia.201900189

5,20-Bis(ethoxycarbonyl)-Substituted Antiaromatic [28]Hexaphyrin and Its Bis-Ni ^II and Bis-Cu ^II Complexes . / Nakai, Akito; Kim, Jinseok; Kim, Dongho et al.
In: Chemistry - An Asian Journal, Vol. 14, No. 7, 01.04.2019, p. 968-971.

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

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N1 - 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

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N2 - 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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