1. Determination of 3(1)-stereochemistry in synthetic bacteriochlorophyll-d homologues and self-aggregation of their zinc complexes.
- Author
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Tamiaki H, Kitamoto H, Nishikawa A, Hibino T, and Shibata R
- Subjects
- Bacteriochlorophylls chemistry, Metals chemistry, Molecular Structure, Organometallic Compounds chemistry, Polymers chemistry, Spectrophotometry, Ultraviolet methods, Stereoisomerism, Bacteriochlorophylls chemical synthesis, Organometallic Compounds chemical synthesis, Zinc chemistry
- Abstract
Zinc complex of methyl 3(1)-octadecyl-bacteriopheophorbide-d was prepared from modification of naturally occurring chlorophyll-a. The 3(1)-epimerically pure samples were obtained by HPLC separation and their stereochemistry including the absolute configuration at the secondary alcoholic 3(1)-position was determined by combination of esterification to methoxy(trifluoromethyl)phenylacetate and NMR spectroscopy (Mosher's method). Both the epimers were monomeric in a polar organic solvent and self-aggregated in a non-polar solvent to give oligomers as well as dimers possessing red-shifted visible absorption bands. Visible spectra of the non-polar organic solutions were dependent upon the 3(1)-chirality and such a diastereoselective control on the self-aggregation led to the formation of self-aggregates with different supramolecular structures.
- Published
- 2004
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