Reaction of meso-Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives

doi:10.6023/cjoc201311039

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 938-947.DOI: 10.6023/cjoc201311039 Previous Articles Next Articles

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meso-焦脱镁叶绿酸-a的化学反应及其叶绿素类二氢卟吩衍生物的合成

徐希森^a, 姚楠楠^a, 刘洋^a, 殷军港^a, 祁彩霞^b, 王进军^a,b

a 烟台大学化学化工学院烟台 264005;
b 山东省黄金工程技术研究中心工业应用烟台 264005

收稿日期:2013-11-23 修回日期:2013-12-30 发布日期:2014-01-22
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
国家自然科学基金（No. 21272048）和山东省黄金工程技术研究中心（2011年度）资助项目.

Reaction of meso-Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives

Xu Xisen^a, Yao Nannan^a, Liu Yang^a, Yin Jungang^a, Qi Caixia^b, Wang Jinjun^a,b

a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
b Shandong Applied Research Centre of Gold Nanotechnology Au-SDARC, Yantai 264005

Received:2013-11-23 Revised:2013-12-30 Published:2014-01-22
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).

meso-Pyropheophorbide-a methyl ester was used as a starting material, and the halogenation and nitration were carried out with different electrophilic reagents making use of active regions in chlorin macrocycle selectively to introduce chlorine, bromine, iodine and nitryl group at 20-meso-position, respectively. The reconstructions for five-membered exocyclic E-ring by allomerization and aminolysis were completed to fuse different azo-heterocycle with the exocyclic ring. The synthesis of 13 unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV-Vis, IR and ¹H NMR spectra. The reaction mechanisms of meso-pyropheophorbide-a and corresponding spectral properties were discussed.

Key words: chlorophyll-a, chlorin, meso-pyropheophorbide, chemical reaction, synthesis

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Xu Xisen, Yao Nannan, Liu Yang, Yin Jungang, Qi Caixia, Wang Jinjun. Reaction of meso-Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chin. J. Org. Chem., 2014, 34(5): 938-947.

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meso-焦脱镁叶绿酸-a的化学反应及其叶绿素类二氢卟吩衍生物的合成

Reaction of meso-Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives

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