Red-Shifted Glycoporphyrins: Synthesis via Sonogashira Cross-Coupling and Studies on Reactive Oxygen Species Production

Glycoporphyrins are in the spotlight as third-generation photosensitizers. Herein, we present a new Sonogashira-based methodology toward C-C-bonded, diverse carbohydrate-porphyrin hybrids. The sugar unit is for the first time effectively conjugated with a porphyrin system, resulting in a bathochromic shift of absorption maxima. The products generate reactive oxygen species with the use of 690-740 nm visible light lamps, making them promising photosensitizers in phototherapies.

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Publication Details

Journal
Organic Letters
Published
2025-07-14
DOI
https://doi.org/10.1021/acs.orglett.5c02038
Primary Topic
Porphyrin and Phthalocyanine Chemistry
Type
article
Field-Weighted Citation Impact
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article

Red-Shifted Glycoporphyrins: Synthesis via Sonogashira Cross-Coupling and Studies on Reactive Oxygen Species Production

Maciej Malinowski, Dariusz Baran
Organic Letters
Porphyrin and Phthalocyanine Chemistry
article

Red-Shifted Glycoporphyrins: Synthesis via Sonogashira Cross-Coupling and Studies on Reactive Oxygen Species Production

Maciej Malinowski, Dariusz Baran
article en

Abstract

Glycoporphyrins are in the spotlight as third-generation photosensitizers. Herein, we present a new Sonogashira-based methodology toward C-C-bonded, diverse carbohydrate-porphyrin hybrids. The sugar unit is for the first time effectively conjugated with a porphyrin system, resulting in a bathochromic shift of absorption maxima. The products generate reactive oxygen species with the use of 690-740 nm visible light lamps, making them promising photosensitizers in phototherapies.

Organic LettersVol. 27(29)
Warsaw University of Technology (PL)
Zero hunger
Openalex Percentile: Top 88%
Porphyrin and Phthalocyanine Chemistry
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