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

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 intramolecul...

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Bibliographic Details
Published in:Chinese chemical letters 2011-05, Vol.22 (5), p.539-542
Main Authors: Li, Cheng Jie, Feng, Ya Qing, Liu, Xiu Jun, Zhang, Tian Yi
Format: Article
Language:English
Subjects:
Anthraquinone
Azo-rearrangement
Fluorescence quenching
IR表征
Porphyrin
偶氮
光谱特性
分子内环化
卟啉蒽醌
合成
荧光光谱
重排
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Summary: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.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2010.11.031