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 | |
| Publication status | Published - 2015 Jun 1 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Organic Chemistry
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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 journal › Article
TY - JOUR
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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U2 - 10.1002/chem.201500650
DO - 10.1002/chem.201500650
M3 - Article
AN - SCOPUS:84930211639
VL - 21
SP - 8341
EP - 8346
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 23
ER -