Abstract
Abstract A zinc bacteriochlorophyll- d analog possessing a fully π-conjugated porphyrin skeleton and an acrylate residue at the 17-position was prepared by chemical modification of an accessory photosynthetic pigment, chlorophyll- c 1 from a diatom Chaetoceros species. The synthetic zinc chlorophyll- c 1 derivative self-aggregated in a less polar organic solvent and in a solid film to give a red-shifted and broadened visible absorption spectrum, which is similar to that of the main light-harvesting antenna of a green photosynthetic bacterium, where magnesium chlorins with the 17-propionate residue including bacteriochlorophyll- d aggregate in a J -type fashion to form large oligomers. The resulting self-aggregates showed specific and intense absorption bands at around 500 and 600 nm due to the π-extension along the molecular x-axis, which could bridge the “green gap” observed in the above natural antenna system. Visible and infrared absorption spectral analyses revealed that the supramolecular structure of self-aggregates of the zinc chlorophyll- c 1 derivative are comparable to those of the natural antenna, in spite of double dehydrogenation at the 17,18- and 17 1 ,17 2 -positions in the molecule.
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