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Synthesis, Photophysical and Electrochemistry of Near-IR Absorbing Bacteriochlorins Related to Bacteriochlorophyll a

  作者 KOZYREV ANDREI; ETHIRAJAN MANIVANNAN; CHEN PING; OHKUBO KEI; ROBINSON BYRON C; BARKIGIA KATHLEEN M; FUKUZUMI SHUNICHI; KADISH KARL M; PANDEY RAVINDRA K  
  选自 期刊  Journal of Organic Chemistry;  卷期  2012年77-22;  页码  10260-10271  
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[摘要]A series of new bacteriochlorins was synthesized using 13(2)-oxo-bacteriopyropheophorbide a (derived from bacteriochlorophyll a) as a starting material, which on reacting with o-phenylenediamine and 1,10-diaminonaphthalene afforded highly conjugated annulated bacteriochlorins with fused quinoxaline, benzimidazole, and perimidine rings, respectively. The absorption spectra of these novel bacteriochlorins demonstrated remarkably red-shifted intense Q(y) absorption bands observed in the range of 816-850 nm with high molar extinction coefficients (89,900- 136,800). Treatment of 13(2)-oxo-bacteriopyropheophorbide a methyl ester with diazomethane resulted in the formation of bacterioverdins containing a fused six-membered methoxy-substituted cyclohexenone (verdin) as an isomeric mixture. The pure isomers which exhibit long-wavelength absorptions in the near-IR region (865-890 nm) are highly stable at room temperature with high reactivity with O-2 at the triplet photoexcited state and favorable redox potential and could be potential candidates for use as photosensitizers in photodynamic therapy (PDT).

 
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