Self-aggregation of zinc bacteriochlorophyll-d analog bearing B-ring reduced chlorin and 17-acrylate residue

Funakoshi, Daichi; Matsubara, Satοshi; Tamiaki, Hitoshi

doi:10.1016/j.tet.2020.131853

Cited by 2 publications

(1 citation statement)

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“…In these studies, the effect of peripheral substituents on the C3 1 -, C7-, C8-, C13 2 -, C17-and C20-positions were widely investigated (Fig. 1A) (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34), and they could influence the supramolecular structures and optical properties of selfassemblies. In many cases, the 3 1 -hydroxy and 13-ketocarbonyl groups, and the coordinated metals (Mg, Zn, Cd) are essential for forming the J-aggregates along the molecular yaxis through hydrogen (3 1 -OH and 13-C=O) and coordination bonding (3 1 -O and M).…”

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confidence: 99%

Synthesis and Self‐Aggregation of Chlorophyll‐a Derivatives Possessing a Hydroxymethyl Group in the C20‐Substituent with Ethynylene and/or Phenylene Linkers

Nakano

Hashimoto

Tamiaki

2022

Photochem & Photobiology

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Chlorophyll(Chl)-a derivatives containing some rigid linkers in the C20 substituents, which were inserted between a hydroxymethyl group and the chlorin p-skeleton, were synthesized and their self-aggregation abilities were investigated. Measurements of electronic absorption, circular dichroism and infrared absorption spectra revealed that the zinc complex of a Chl-a derivative bearing a (p-ethynyl)benzyl alcoholic moiety at the C20-position gave its J-aggregates in an aqueous micellar solution through the hydrogen and coordination bonding. These results exhibited the potential of Chl-a derivatives bearing a hydroxyl group in the C20 substituents as the model compounds for chlorosomal light-harvesting antennas.

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