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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 11: 2357 - 2366

DOI: https://doi.org/10.6023/cjoc201305006

Articles

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

  • Liang Boying ,
  • Liu Yang ,
  • Xu Xisen ,
  • Jin Yingxue ,
  • Qi Caixia ,
  • Wang Jinjun
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  • 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 date: 2013-05-03

  Revised date: 2013-07-14

  Online 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).

Fold

Abstract

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]. Chinese Journal of Organic Chemistry, 2013 , 33(11) : 2357 -2366 . DOI: 10.6023/cjoc201305006

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