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Self-aggregation of synthetic zinc chlorophyll derivative possessing a perfluoroalkyl group in a fluorinated solvent
Reiko Shibata1, Hitoshi Tamiaki
1Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.
Abstract:
Zinc 3(1)-hydroxy-13(1)-oxo-chlorin possessing a perfluoroheptyl group on the 17-propionate was prepared by modifying chlorophyll a. The synthetic compound self-aggregated in 0.1% (v/v) THF and HCFC225cb (CClF2CF2CHClF) to give similar large oligomers to natural light-harvesting antennae of green photosynthetic bacteria and their models. Visible absorption, circular dichroism, and fluorescence emission spectra showed that F-F interaction between the perfluoroheptyl side chain and the fluorinated solvent (HCFC225cb) stabilized the supramolecular structure. The core part of the supramolecular structure was constructed by a special bond of Zn...O3(1)-H...O=C13(1) and pi-pi stacking, and the 17-propionates were at the peripheral part.
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