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 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Organic Chemistry
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Soya, T., Kim, W., Kim, D., & Osuka, A. (2015). Stable [48]-, [50]-, and [52]dodecaphyrins(1.1.0.1.1.0.1.1.0.1.1.0): The largest Hückel aromatic molecules. Chemistry - A European Journal, 21(23), 8341-8346. https://doi.org/10.1002/chem.201500650