Synthesis of a chlorophyll-a derivative fused with an additional exo-five-membered ring and its optical properties |
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Affiliation: | 1. Guangzhou Institute of Geochemistry, Chinese Academy of Sciences, Guangzhou, China;2. State Key Laboratory of Tropical Oceanography, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China;3. University of Chinese Academy of Sciences, Beijing, China |
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Abstract: | A C20-free chlorophyll-a derivative with an additional exo-five-membered ring was successfully prepared using an ethylene linkage at the C3- and C5-positions. A bromination at the C20-position was requisite for the cyclization of a 1-hydroxyethyl or vinyl group at the C3-position of methyl bacteriopheophorbide-d or methyl pyropheophorbide-a, respectively. By comparing optical properties of the cyclized product with those of its 3-ethyl uncyclized analog in a diluted dichloromethane solution, it was shown that the cyclization shifted the Qx and Bx absorption maxima to longer wavelengths and reduced the Stokes shift. |
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Keywords: | Acidic cyclization Ethylene linkage Fused ring Pyropheophorbide |
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