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. 2024 Mar;23(3):421-434.
doi: 10.1007/s43630-023-00528-9. Epub 2024 Jan 24.

Supramolecular chirality in self-assembly of zinc protobacteriochlorophyll-d analogs possessing enantiomeric esterifying groups

Mizuki Yasui  1 , Hitoshi Tamiaki  2
Affiliations

Supramolecular chirality in self-assembly of zinc protobacteriochlorophyll-d analogs possessing enantiomeric esterifying groups

Mizuki Yasui et al. Photochem Photobiol Sci. 2024 Mar.

Abstract

Zinc 3-hydroxymethyl-pyroprotopheophorbides-a esterified with a chiral secondary alcohol at the 17-propionate residue were prepared as bacteriochlorophyll-d analogs. The synthetic zinc 31-hydroxy-131-oxo-porphyrins self-aggregated in an aqueous Triton X-100 micellar solution to give red-shifted and broadened Soret and Qy absorption bands in comparison with their monomeric bands. The intense, exciton-coupled circular dichroism spectra of their self-aggregates were dependent on the chirality of the esterifying groups. The observation indicated that the self-aggregates based on the J-type stacking of the porphyrin cores were sensitive to the peripheral 17-propionate residues. The supramolecular structures of the present J-aggregates as models of bacteriochlorophyll aggregates in natural chlorosomes were remotely regulated by the esterifying groups.

Keywords: Chlorosome; Circular dichroism; Porphyrin; Self-aggregation; Substitution effect.

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