Self-aggregation of Synthetic 20-<i>O</i>-Substituted Bacteriochlorophyll-<i>d</i> Analogs

Sakaguchi, Kana; Kishi, Masashi; Tamiaki, Hitoshi

doi:10.1246/cl.210216

Cited by 3 publications

(1 citation statement)

References 31 publications

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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).…”

Section: Introductionmentioning

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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Section: Introductionmentioning

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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Self-aggregation behavior of dimeric chlorophyll-a derivatives linked with ethynylene and m-phenylene moieties

Hisahara,

Nakano,

Tamiaki

2023

Photochem Photobiol Sci

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Self-aggregation of synthetic zinc 3-hydroxymethyl-chlorophyll-a derivatives possessing electron-withdrawing groups at the 20-position in aqueous micelle solution

Sakaguchi

Kishi

Kinoshita

et al. 2021

J. Porphyrins Phthalocyanines

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Zinc methyl 3-hydroxymethyl-pyropheophorbides-[Formula: see text] bearing an acetyl or nitro group at the 20-position were prepared by chemically modifying natural chlorophyll-[Formula: see text]. The synthetic zinc 20-substituted bacteriochlorophyll-[Formula: see text] analogs self-aggregated in an aqueous Triton X-100 micelle solution to give red-shifted and broadened electronic absorption bands, similarly as in one of the photosynthetic light-harvesting antennas, chlorosomes. Although the sterically bulky 20-substituents of the semisynthetic zinc 31-hydroxy-131-oxo-chlorins partially disturbed the chlorosomal self-aggregates which would be produced by the [Formula: see text]–[Formula: see text] stacking of the chlorin chromophores, their electron-withdrawing abilities should enhance the specific, intermolecular interaction of Zn[Formula: see text]O32–H[Formula: see text]O=C-13 which was essential for the chlorosomal self-aggregation. Such self-assemblies using these model pigments would provide a new clue for constructing of artificial photosynthetic systems.

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Self-aggregation of Synthetic 20-O-Substituted Bacteriochlorophyll-d Analogs

Cited by 3 publications

References 31 publications

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

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

Self-aggregation behavior of dimeric chlorophyll-a derivatives linked with ethynylene and m-phenylene moieties

Self-aggregation of synthetic zinc 3-hydroxymethyl-chlorophyll-a derivatives possessing electron-withdrawing groups at the 20-position in aqueous micelle solution

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