Abstract
Zinc complexes of 3-hydroxymethyl-131-oxo-chlorins possessing a vinyl or its trans-substituted group at the 20-position were prepared through regioselective bromination and successive palladium-catalyzed cross-coupling reactions from naturally occurring chlorophyll-a. The synthetic zinc chlorophyll-a derivatives self-aggregated in an aqueous Triton X-100 micelle solution to give red-shifted and broadened electronic absorption bands, which were similar to those of bacteriochlorophyll-c/d self-aggregates in the main light-harvesting antenna systems of green photosynthetic bacteria. Because of the sterically demanded perpendicular orientation of the (un)substituted ethenyl group to the chlorin π-system, the present model compounds had less J-aggregation ability in a slipped π–π interaction fashion than the corresponding saturated ethyl-type analogs, while halogenations at the terminal of the 20-vinyl group enhanced the ability due to their electron-withdrawing effect.
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