TY - JOUR
T1 - Synthesis, photophysical and electrochemistry of near-IR absorbing bacteriochlorins related to bacteriochlorophyll a
AU - Kozyrev, Andrei
AU - Ethirajan, Manivannan
AU - Chen, Ping
AU - Ohkubo, Kei
AU - Robinson, Byron C.
AU - Barkigia, Kathleen M.
AU - Fukuzumi, Shunichi
AU - Kadish, Karl M.
AU - Pandey, Ravindra K.
PY - 2012/11/16
Y1 - 2012/11/16
N2 - 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 Qy absorption bands observed in the range of 816-850 nm with high molar extinction coefficients (89,900-136,800). Treatment of 132-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).
AB - 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 Qy absorption bands observed in the range of 816-850 nm with high molar extinction coefficients (89,900-136,800). Treatment of 132-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).
UR - http://www.scopus.com/inward/record.url?scp=84869201865&partnerID=8YFLogxK
U2 - 10.1021/jo301895p
DO - 10.1021/jo301895p
M3 - Article
C2 - 23082726
AN - SCOPUS:84869201865
SN - 0022-3263
VL - 77
SP - 10260
EP - 10271
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 22
ER -