Citation: Cheng Jie Li, Ya Qing Feng, Xiu Jun Liu, Tian Yi Zhang. The synthesis of porphyrin-anthraquinone dyad via an azo-rearrangement[J]. Chinese Chemical Letters, ;2011, 22(5): 539-542. doi: 10.1016/j.cclet.2010.11.031 shu

The synthesis of porphyrin-anthraquinone dyad via an azo-rearrangement

School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China

Received Date: 30 August 2010

Fund Project: Natural Science Foundation of Tianjin (No.10JCZDJC23700) and Independent Innovation Foundation of Tianjin University (2010)This work is financially supported by National Natural Science Foundation of China (No.21076147)

One novel porphyrin p-Q2 is planned to be synthesized by condensation between ATPP and Q1.However, after separation by chromatography and characterization with IR, ¹H NMR, HR-MS and X-ray, p-Q1 is obtained unexpectedly.Compared the structure of p-Q1 with that of p-Q2, it is realized that an intramolecular cyclization rearrangement takes place when the azo group is situated in the o-position to the amido group.This rearrangement offers a new way to prepare indazole heterocycle.In addition, the spectral properties of p-Q1 have been studied by UV-vis and steady state fluorescence spectroscopy.Strong fluorescence quenching is observed in the preliminary emission spectrum due to the proposed electron transfer from the excited porphyrin to the anthraquinone moieties.
- Porphyrin,
- Anthraquinone,
- Azo-rearrangement,
- Fluorescence quenching
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