Modifications for Peripheral Structures of Purpurin-18 and Synthesis of Chlorophyllous Chlorin Derivatives

doi:10.6023/cjoc201305006

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (11): 2357-2366.DOI: 10.6023/cjoc201305006 Previous Articles Next Articles

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红紫素-18的周环结构修饰及其叶绿素类二氢卟吩衍生物的合成

梁波颖^a, 刘洋^b, 徐希森^b, 金英学^a, 祁彩霞^c, 王进军^b,c

a 哈尔滨师范大学化学化工学院哈尔滨 150025;
b 烟台大学化学化工学院烟台 264005;
c 山东省黄金工程技术研究中心工业应用烟台 264005

收稿日期:2013-05-03 修回日期:2013-07-14 发布日期:2013-07-19
通讯作者: 金英学，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.

Modifications for Peripheral Structures of Purpurin-18 and Synthesis of Chlorophyllous Chlorin Derivatives

Liang Boying^a, Liu Yang^b, Xu Xisen^b, Jin Yingxue^a, Qi Caixia^c, Wang Jinjun^b,c

a College of Chemistry & Chemical Engineering, Harbin Normal University, Harbin 150025;
b College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
c Shandong Applied Research Centre of Gold Nanotechnology Au-SDARC, Yantai 264005

Received:2013-05-03 Revised:2013-07-14 Published:2013-07-19
Supported by:
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nano-technology (2011).

Purpurin-18 methyl ester was used as a starting material, and the modifications for the structure on the terminal of its N²¹-N²³-axis were completed making use of electron-richous properties of C (3)-vinyl group by various reactions including oxidation, reduction, electrophilic addition and 1, 3-polar cycloaddition. The substituted groups, which could conjugated with macrocyclic chromophore in different form, were introduce to 3-position on the periphery, respectively. The synthesis of 11 unreported chlorophyllous chlorins with basic skeloton of purpurin-18 was accomplished and their chemical structures were characterized by elemental analysis, UV, IR and ¹H NMR spectra. The influence of peripheric structure of purpurin-18 on their electronic spectrum was discussed and the possible mechanisms about corresponding reactions were tentatively proposed.

Key words: chlorophyll-a, chlorin, purpurin-18, chemical modification, synthesis

Cite this article

Liang Boying, Liu Yang, Xu Xisen, Jin Yingxue, Qi Caixia, Wang Jinjun. Modifications for Peripheral Structures of Purpurin-18 and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chin. J. Org. Chem., 2013, 33(11): 2357-2366.

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红紫素-18的周环结构修饰及其叶绿素类二氢卟吩衍生物的合成

Modifications for Peripheral Structures of Purpurin-18 and Synthesis of Chlorophyllous Chlorin Derivatives

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