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• W2022286848 abstract "Bacteriochlorins (tetrahydroporphyrins) are attractive for diverse photochemical applications owing to their strong absorption in the near-infrared spectral region, as exemplified by the bacterial photosynthetic pigment bacteriochlorophyll a, yet often are labile toward dehydrogenation to give the chlorin. Tetradehydrocorrins (ring-contracted tetrahydroporphyrins) are attractive for studies of catalysis analogous to that of vitamin B12. An eight-step synthesis toward such tetrahydroporphyrinic macrocycles begins with p-tolualdehyde and proceeds to a dihydrodipyrrin-acetal (1) bearing a geminal dimethyl group and a p-tolyl substituent. Self-condensation of 1 in CH3CN containing BF3·OEt2 at room temperature afforded a readily separable mixture of two free base bacteriochlorins and a free base B,D-tetradehydrocorrin. Each bacteriochlorin contains two geminal dimethyl groups to lock-in the bacteriochlorin hydrogenation level, p-tolyl substituents at opposing (2,12) β-positions, and the absence (H−BC) or presence (MeO−BC) of a methoxy group at the 5- (meso) position. The B,D-tetradehydrocorrin (TDC) lies equidistant between the hydrogenation levels of corrin and corrole, is enantiomeric, and contains two geminal dimethyl groups, 2,12-di-p-tolyl substituents, and an acetal group at the pyrroline−pyrrole junction. Examination of the effect of the concentrations of 1 (2.5−50 mM) and BF3·OEt2 (10−500 mM) revealed a different response surface for each of H−BC, MeO−BC, and TDC, enabling relatively selective preparation of a given macrocycle. The highest isolated yield of each was 49, 30, and 66%, respectively. The macrocycles are stable to routine handling in light and air. The bacteriochlorins display characteristic spectral features; for example, H−BC exhibits near-IR absorption (λQy = 737 nm, εQy = 130 000 M-1 cm-1) and emission (λem = 744 nm, Φf = 0.14). In summary, this simple entry to stable bacteriochlorins and tetradehydrocorrins should facilitate a wide variety of applications." @default.
• W2022286848 created "2016-06-24" @default.
• W2022286848 creator A5003916317 @default.
• W2022286848 creator A5083917347 @default.
• W2022286848 date "2005-06-07" @default.
• W2022286848 modified "2023-10-10" @default.
• W2022286848 title "De Novo Synthesis of Stable Tetrahydroporphyrinic Macrocycles: Bacteriochlorins and a Tetradehydrocorrin" @default.
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• W2022286848 doi "https://doi.org/10.1021/jo050467y" @default.
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