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



杨泽a, 王振a, 刘洋a, 徐希森a, 祁彩霞a, 王进军b   

  1. 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
  • 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 Zea, Wang Zhena, Liu Yanga, Xu Xisena, Qi Caixiaa, Wang Jinjunb   

  1. 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