Synthesis of (Pyro)pheophorbide Derivatives with Long Wavelength Absorption and Their Electronic Spectra

doi:10.6023/cjoc201209009

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (01): 116-124.DOI: 10.6023/cjoc201209009 Previous Articles Next Articles

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具有长波吸收的(焦)脱镁叶绿酸衍生物的合成及其电子光谱

杨泽^a, 王振^a, 刘洋^a, 徐希森^a, 祁彩霞^a, 王进军^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:2012-09-06 修回日期:2012-09-23 发布日期:2012-10-11
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
中匈政府间科技合作(No. 2008-333-4-32 )和山东黄金工程技术研究中心(2011年度)资助项目.

Synthesis of (Pyro)pheophorbide Derivatives with Long Wavelength Absorption and Their Electronic Spectra

Yang Ze^a, Wang Zhen^a, Liu Yang^a, Xu Xisen^a, Qi Caixia^a, Wang Jinjun^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:2012-09-06 Revised:2012-09-23 Published:2012-10-11
Supported by:
Project supported by the Technology Cooperation between Governments of China and Hungary and the Shandong Applied Research Centre of Gold Nanotechnology (2011).

Methyl pheophorbide-a and b were used as starting material. The different carbonyl groups were built along the periphery of methyl pheophorbide-a by modifing for C(3)-vinyl group, exocyclic E-ring and 20-meso-position. Making use of these carbonyl groups or original C(7)-formyl group of pheophorbide-b introduced β,β-dicyanomethylene moiety at different positions by Knoevenagel condensation with malononitrile to synthesize a series of chlorophyllous chlorin derivatives with long wavelength absorption. The effect on the electronic spectra and chemical activities of macrocycle molecule due to introduction of β,β-dicyanomethylene moiety were discussed, and the possible mechanisms about corresponding reactions were tentatively proposed. The structures of all new chlorin derivatives were characterized by ¹H NMR, UV, IR spectra and elemental analysis.

Key words: chlorophyll, (pyro)pheophorbide, chlorin, synthesis, electronic spectra

Cite this article

Yang Ze, Wang Zhen, Liu Yang, Xu Xisen, Qi Caixia, Wang Jinjun. Synthesis of (Pyro)pheophorbide Derivatives with Long Wavelength Absorption and Their Electronic Spectra[J]. Chin. J. Org. Chem., 2013, 33(01): 116-124.

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具有长波吸收的(焦)脱镁叶绿酸衍生物的合成及其电子光谱

Synthesis of (Pyro)pheophorbide Derivatives with Long Wavelength Absorption and Their Electronic Spectra

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