期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 22, 页码 10260-10271出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo301895p
关键词
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资金
- NIH [CA127369, CA55791]
- Robert A. Welch Foundation [E-680]
- Global COE from the Ministry of Education, Culture, Sports, Science and Technology, Japan
- KOSEF/MEST through WCU, Korea [R31-2008-000-10010-0]
- Center for Research Resources of the NIH
- Office of Biological and Environmental Research and Basic Energy Sciences of the U.S. Department of Energy [20108010, 23750014]
- Grants-in-Aid for Scientific Research [23750014, 20108010] Funding Source: KAKEN
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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