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1 January 2005 Self-aggregation of Synthetic Protobacteriochlorophyll-d Derivatives
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Abstract

31-Racemically pure zinc 31-hydroxy-131-oxo-porphyrins (zinc methyl 17,18-dehydro-bacteriopheophorbides-d) as well as their 31-demethyl form were prepared by modifying chlorophyll-a through oxidation by 2,3-dichloro-5,6-dicyano-benzoquinone. From visible, circular dichroism and infrared spectral analyses, these synthetic pigments self-aggregated in 1%(vol/vol) tetrahydrofuran and cyclohexane to give large oligomers by an intermolecular bonding of 13-C=O⋯H–O(31)⋯Zn(central) and π–π interaction of the porphyrin chromophores. The supramolecular structures are similar to those of the corresponding chlorins and a core part of extramembranous light-harvesting antennas of photosynthetic green bacteria. The 17,18-dehydrogenation of a chlorin to porphyrin moiety did not disturb its self-aggregation, and the synthetic zinc porphyrins are good models for naturally occurring, self-aggregative bacteriochlorophylls.

Hitoshi Tamiaki, Hiroyuki Kitamoto, Takuya Watanabe, and Reiko Shibata "Self-aggregation of Synthetic Protobacteriochlorophyll-d Derivatives," Photochemistry and Photobiology 81(1), 170-176, (1 January 2005). https://doi.org/10.1562/2004-08-02-RA-254.1
Received: 31 July 2004; Accepted: 1 October 2004; Published: 1 January 2005
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