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Self-aggregation of 32-substituted bacteriochlorophyll-d analogs in aqueous micelle

    https://doi.org/10.1142/S1088424622500675Cited by:4 (Source: Crossref)

    As naturally occurring bacteriochlorophyll-d models, zinc methyl (31R)-bacteriopheophorbides-d possessing ethyl, vinyl, and ethynyl groups at the 32-position were prepared by chemically modifying chlorophyll-a. The synthetic molecules self-aggregated in an aqueous Triton X-100 micelle solution similarly as in the major light-harvesting antenna of photosynthetic green bacteria to give supramolecularly ordered large oligomers with red-shifted and broadened visible absorption bands, compared with the monomeric bands. The sequential hydrogenation of the 32-ethynyl to ethyl group via the vinyl group gradually suppressed the chlorosomal self-aggregation ability. The successive elongation of the 31-alkyl chain from a methyl to propyl group via an ethyl group also diminished the J-aggregation ability. These decreases in the self-aggregation were ascribable to the steric enhancement of the 32-substituents near the 31-hydroxy group requisite for the J-aggregation.

    Dedicated to Prof. Tomás Torres on the occasion of his 70th birthday

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