Synthesis of monovinyl- and divinyl-chlorophyll analogs and their physical properties

Kim, Kifa; Tsuji, Katsunori; Kinoshita, Yusuke; Miyatake, Tomohiro; Tamiaki, Hitoshi

doi:10.1016/j.tet.2016.12.003

Cited by 7 publications

(1 citation statement)

References 33 publications

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“…In addition to the aforementioned Chls possessing vinyl groups, many vinyl‐chlorins have been prepared by chemically modifying natural Chls, and their physical properties have been investigated. In a series of (zinc) methyl pyropheophorbides, a vinyl (or methylene) group was substituted at the 3‐, 7‐, 8‐ (20), 12‐ (21,22), 13 1 ‐ (23), 13 2 ‐ (24), and 20‐positions (25) (see Fig. 1B), and their physical properties were compared with those of the unsubstituted, methylated, and ethylated counterparts.…”

Section: Introductionmentioning

confidence: 99%

Substituted Methylenation at the 13²‐Position of a Chlorophyll‐a Derivative via Mixed Aldol Condensation, Optical Properties of the Synthetic Bacteriochlorophyll‐d Analogs, and Self‐aggregation of Their Zinc Complexes^†

Takeda

Kitagawa

Tamiaki

2022

Photochem & Photobiology

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Chlorophyll-a derivatives possessing a substituted methylene group at the 13 2 -position were prepared by the mixed aldol condensation of methyl 3-hydroxymethyl-pyropheophorbide-a with aldehydes bearing a methyl, p-nitro/cyanophenyl, or pentafluorophenyl group. Their electronic absorption spectra were dependent on the substituents at the methylene terminal. The Soret bands were broadened by increasing the group electronegativity of the substituents, which was ascribable to the charge transfer from the core chlorin to the peripheral substituent in a molecule. Although their Qy absorption and fluorescence emission bands resembled each other, the emission intensities decreased with an increase in the electronegativity because of intramolecular electron transfer quenching. Some of their zinc complexes self-aggregated in a less polar organic solvent to give red-shifted and broadened absorption bands with intense circular dichroism couplets, which were similar to those of bacteriochlorophyll-c/d aggregates in natural chlorosomes as the main lightharvesting antennas of green photosynthetic bacteria and their models. The J-aggregation was suppressed with an enhancement in the size of the 13 2 -substituents.

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Section: Introductionmentioning

confidence: 99%

Substituted Methylenation at the 13²‐Position of a Chlorophyll‐a Derivative via Mixed Aldol Condensation, Optical Properties of the Synthetic Bacteriochlorophyll‐d Analogs, and Self‐aggregation of Their Zinc Complexes^†

Takeda

Kitagawa

Tamiaki

2022

Photochem & Photobiology

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Chlorophylls

Tamiaki

2022

Fundamentals of Porphyrin Chemistry

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In vivo and in vitro preparation of divinyl-132,173-cyclopheophorbide-a enol

Kinoshita

Kayama

Kashiyama

et al. 2018

Bioorganic & Medicinal Chemistry Letters

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Synthesis of monovinyl- and divinyl-chlorophyll analogs and their physical properties

Cited by 7 publications

References 33 publications

Substituted Methylenation at the 13²‐Position of a Chlorophyll‐a Derivative via Mixed Aldol Condensation, Optical Properties of the Synthetic Bacteriochlorophyll‐d Analogs, and Self‐aggregation of Their Zinc Complexes^†

Substituted Methylenation at the 13²‐Position of a Chlorophyll‐a Derivative via Mixed Aldol Condensation, Optical Properties of the Synthetic Bacteriochlorophyll‐d Analogs, and Self‐aggregation of Their Zinc Complexes^†

Chlorophylls

In vivo and in vitro preparation of divinyl-132,173-cyclopheophorbide-a enol

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Synthesis of monovinyl- and divinyl-chlorophyll analogs and their physical properties

Cited by 7 publications

References 33 publications

Substituted Methylenation at the 132‐Position of a Chlorophyll‐a Derivative via Mixed Aldol Condensation, Optical Properties of the Synthetic Bacteriochlorophyll‐d Analogs, and Self‐aggregation of Their Zinc Complexes†

Substituted Methylenation at the 132‐Position of a Chlorophyll‐a Derivative via Mixed Aldol Condensation, Optical Properties of the Synthetic Bacteriochlorophyll‐d Analogs, and Self‐aggregation of Their Zinc Complexes†

Chlorophylls

In vivo and in vitro preparation of divinyl-132,173-cyclopheophorbide-a enol

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Substituted Methylenation at the 13²‐Position of a Chlorophyll‐a Derivative via Mixed Aldol Condensation, Optical Properties of the Synthetic Bacteriochlorophyll‐d Analogs, and Self‐aggregation of Their Zinc Complexes^†

Substituted Methylenation at the 13²‐Position of a Chlorophyll‐a Derivative via Mixed Aldol Condensation, Optical Properties of the Synthetic Bacteriochlorophyll‐d Analogs, and Self‐aggregation of Their Zinc Complexes^†