Stable [48]-, [50]-, and [52]dodecaphyrins(1.1.0.1.1.0.1.1.0.1.1.0): The largest Hückel aromatic molecules

Takanori Soya; Woojae Kim; Dongho Kim; Atsuhiro Osuka

doi:10.1002/chem.201500650

Stable [48]-, [50]-, and [52]dodecaphyrins(1.1.0.1.1.0.1.1.0.1.1.0): The largest Hückel aromatic molecules

Takanori Soya, Woojae Kim, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

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

23 Citations (Scopus)

Abstract

[52]Dodecaphyrin(1.1.0.1.1.0.1.1.0.1.1.0) was quantitatively oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the corresponding [50]dodecaphyrin. Further oxidation of [50]dodecaphyrin with MnO₂ quantitatively afforded [48]dodecaphyrin. Of the three, [50]dodecaphyrin showed Hückel aromatic character as the largest aromatic molecule reported to date. Protonation of [50]dodecaphyrin with methanesulfonic acid (MSA) led to the formation of a planar tetraprotonated species that displayed a sharp and intense Soret-like band at 906 nm with ε=6.5×10⁵ M^-1 cm^-1 and Q-band-like bands at 1346 and 1600 nm.

Original language	English
Pages (from-to)	8341-8346
Number of pages	6
Journal	Chemistry - A European Journal
Volume	21
Issue number	23
DOIs	https://doi.org/10.1002/chem.201500650
Publication status	Published - 2015 Jun 1

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Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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title = "Stable [48]-, [50]-, and [52]dodecaphyrins(1.1.0.1.1.0.1.1.0.1.1.0): The largest H{\"u}ckel aromatic molecules",

abstract = "[52]Dodecaphyrin(1.1.0.1.1.0.1.1.0.1.1.0) was quantitatively oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the corresponding [50]dodecaphyrin. Further oxidation of [50]dodecaphyrin with MnO2 quantitatively afforded [48]dodecaphyrin. Of the three, [50]dodecaphyrin showed H{\"u}ckel aromatic character as the largest aromatic molecule reported to date. Protonation of [50]dodecaphyrin with methanesulfonic acid (MSA) led to the formation of a planar tetraprotonated species that displayed a sharp and intense Soret-like band at 906 nm with ε=6.5×105 M-1 cm-1 and Q-band-like bands at 1346 and 1600 nm.",

author = "Takanori Soya and Woojae Kim and Dongho Kim and Atsuhiro Osuka",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

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doi = "10.1002/chem.201500650",

language = "English",

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T1 - Stable [48]-, [50]-, and [52]dodecaphyrins(1.1.0.1.1.0.1.1.0.1.1.0)

T2 - The largest Hückel aromatic molecules

AU - Soya, Takanori

AU - Kim, Woojae

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2015/6/1

Y1 - 2015/6/1

N2 - [52]Dodecaphyrin(1.1.0.1.1.0.1.1.0.1.1.0) was quantitatively oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the corresponding [50]dodecaphyrin. Further oxidation of [50]dodecaphyrin with MnO2 quantitatively afforded [48]dodecaphyrin. Of the three, [50]dodecaphyrin showed Hückel aromatic character as the largest aromatic molecule reported to date. Protonation of [50]dodecaphyrin with methanesulfonic acid (MSA) led to the formation of a planar tetraprotonated species that displayed a sharp and intense Soret-like band at 906 nm with ε=6.5×105 M-1 cm-1 and Q-band-like bands at 1346 and 1600 nm.

AB - [52]Dodecaphyrin(1.1.0.1.1.0.1.1.0.1.1.0) was quantitatively oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the corresponding [50]dodecaphyrin. Further oxidation of [50]dodecaphyrin with MnO2 quantitatively afforded [48]dodecaphyrin. Of the three, [50]dodecaphyrin showed Hückel aromatic character as the largest aromatic molecule reported to date. Protonation of [50]dodecaphyrin with methanesulfonic acid (MSA) led to the formation of a planar tetraprotonated species that displayed a sharp and intense Soret-like band at 906 nm with ε=6.5×105 M-1 cm-1 and Q-band-like bands at 1346 and 1600 nm.

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Stable [48]-, [50]-, and [52]dodecaphyrins(1.1.0.1.1.0.1.1.0.1.1.0): The largest Hückel aromatic molecules

Abstract

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