Dodecaphyrin(18.104.22.168.22.214.171.124.0.1.1.0) was quantitatively oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the corresponding dodecaphyrin. Further oxidation of dodecaphyrin with MnO2 quantitatively afforded dodecaphyrin. Of the three, dodecaphyrin showed Hückel aromatic character as the largest aromatic molecule reported to date. Protonation of 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.
All Science Journal Classification (ASJC) codes
- Organic Chemistry