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

Author:

Tani Shunsuke1,Kanehisa Seiji1,Tamiaki Hitoshi1

Affiliation:

1. Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan

Abstract

As naturally occurring bacteriochlorophyll-[Formula: see text] models, zinc methyl (3[Formula: see text]-bacteriopheophorbides-[Formula: see text] possessing ethyl, vinyl, and ethynyl groups at the 32-position were prepared by chemically modifying chlorophyll-[Formula: see text]. 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 [Formula: see text]-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 [Formula: see text]-aggregation.

Funder

JSPS KAKENHI

Scientific Research

Publisher

World Scientific Pub Co Pte Ltd

Subject

General Chemistry

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