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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 01: 149 - 155

DOI: https://doi.org/10.6023/cjoc1106303

Articles

Synthesis of Chlorphyll-a Derivatives Substituted with β,β-Dicyanomethylene and Their Visible Spectra

  • WU Jin ,
  • YIN Jun-Gang ,
  • LIU Ran-Ran ,
  • YANG Ze ,
  • WANG Zhen ,
  • WANG Jin-Jun
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  • a Colledge of College of Pharmacy, Yantai University, Yantai 264005;
    b Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received date: 2011-06-30

  Revised date: 2011-08-24

  Online published: 2011-09-28

Supported by

Project supported by Natural Science Foundation of Shandong Province (No. Y2008B49).

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Abstract

Using methyl pyropheophorbide-a as starting material, the carbonyl structures were constructed in different positions of the chlorin periphery by oxidition of the 3-vinyl group, Grignard reaction and air oxidation and rearrangement of E-ring. Then the synthesis of chlorphyll-a derivatives substituted with β,β-dicyanomethylene having long wavelength absorption property was accomplished by Knoevenagel reaction of the carbonyl group on the chromophore with malononitrile. The effect of the peripheral conjugated substitutes oriented in different directions on the visible spectra was also discussed. The structures of all new chlorine derivatives were characterized by elemtntal analysis, UV, IR and 1H NMR spectra.

Key words： methyl pyropheophorbide-a; chlorophyll-a derivative; synthesis; visible spectra; photodynamic therapy

Cite this article

WU Jin , YIN Jun-Gang , LIU Ran-Ran , YANG Ze , WANG Zhen , WANG Jin-Jun . Synthesis of Chlorphyll-a Derivatives Substituted with β,β-Dicyanomethylene and Their Visible Spectra[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 149 -155 . DOI: 10.6023/cjoc1106303

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