Preparation of mono-vinylated and formylated chlorophyll derivatives and their optical properties
2016
Tamiaki, Hitoshi | Tsuji, Kazuki | Kim, Kifa | Miyatake, Tomohiro
Regioisomeric 3- and 8-vinylchlorins as well as 7- and 12-vinylchlorins were prepared by modifying naturally occurring chlorophylls-a and/or b. The corresponding formylchlorins were synthesized by oxidation of the 3/8-vinyl, 7-hydroxymethyl or 12-methyl groups and readily transformed to the vinylchlorins by Wittig reactions. Their visible absorption, circular dichroism, fluorescence emission spectra in dichloromethane were dependent on the substituents directly conjugated with a chlorin π-system. The substitution with vinyl and formyl groups at the 3- and 12-positions on a molecular y-axis shifted redmost Qy absorption maxima to longer wavelengths than those at 7/8-positions on an x-axis. The synthetic vinylchlorins were more fluorescent than the corresponding formylchlorins.
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