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

Research output: Contribution to journalArticle

19 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 languageEnglish
Pages (from-to)8341-8346
Number of pages6
JournalChemistry - A European Journal
Volume21
Issue number23
DOIs
Publication statusPublished - 2015 Jun 1

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Protonation
Oxidation
Molecules
Acids
methanesulfonic acid
dichlorodicyanobenzoquinone

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

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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",
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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. / Soya, Takanori; Kim, Woojae; Kim, Dongho; Osuka, Atsuhiro.

In: Chemistry - A European Journal, Vol. 21, No. 23, 01.06.2015, p. 8341-8346.

Research output: Contribution to journalArticle

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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

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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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