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Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 5: 1060 - 1068

DOI: https://doi.org/10.6023/cjoc201408009

ARTICLE

Transformation for Exocyclic Ring of Pheophorbide and Syn-thesis of Chlorophyllous Degradation Derivatives

  • Zhang Shanguo ,
  • Li Jiazhu ,
  • Zhang Peng ,
  • Qi Caixia ,
  • Wang Jinjun
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  • a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Wenjing College, Yantai University, Yantai 264005;
    c Shandong Applied Research Centre of Gold Nanotechnology Au-SDARC, Yantai 264005

Received date: 2014-08-09

  Revised date: 2014-10-23

  Online published: 2015-01-06

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).

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Abstract

From pheophorbide-a methyl ester, the substituted groups with aromatic ring, which can conjugated with chromophore in different forms, were established at 3-, 12- and 20-position on the chlorin periphery by some classic reactions such as 1,3-dipolar cycloaddition, radical substitution and Wittig olefin-forming. The transformations in the exocyclic ring to other chlorophyllous degradation structures were carried out making use of allomerization, condensation and rearrangement reac-tions. A series of unreported new chlorins were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. In the same time the chemical reaction process around the periphery, the conjugated effect about the aromatic substitutes and the varying law about electronic spectra of the macrocyclic molecule were also discussed.

Key words： chlorophyll-a; chlorin; transformation for exocyclic ring; chlorophyllous degradation derivative; chemical reaction

Cite this article

Zhang Shanguo , Li Jiazhu , Zhang Peng , Qi Caixia , Wang Jinjun . Transformation for Exocyclic Ring of Pheophorbide and Syn-thesis of Chlorophyllous Degradation Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 1060 -1068 . DOI: 10.6023/cjoc201408009

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