ArticleJournal of the American Chemical Society2024
Thermal Truncation of Heptamethine Cyanine Dyes.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- π-Extended COUPY Fluorophores for Targeted Near-Infrared Fluorescence and Lifetime Imaging in Live Cells.Angewandte Chemie (International ed. in English) · 2026Article
- Experimental Study Redefines the Mechanism of Heptamethine Cyanine Phototruncation.Journal of the American Chemical Society · 2026Article
- Photophysics of Organic Fluorophore Photobluing and Its Applications in Fluorescence and Super-Resolution Microscopy.Accounts of chemical research · 2026Article
- π-Extended Ru-COUBPY Photosensitizers forJournal of the American Chemical Society · 2025Article
- Cyanines Substituted on the Polymethine Chain: Synthesis, Resulting Properties, and Application Use Cases.ChemPlusChem · 2025Review
- Time-Resolved Fluorescence Detection of Nicked DNA via Site-Specific Stacking of Sulfo-Cy3: The Role of Charge, Polarity, Linker, and Sequence Context.The journal of physical chemistry. B · 2025Article
- High-Resolution Multicolor Shortwave Infrared DynamicJournal of the American Chemical Society · 2025Article
- Achieving Olympicene Functionalization Three Ways.The Journal of organic chemistry · 2025Article
- Indocarbocyanine-Indodicarbocyanine (sCy3-sCy5) Absorptive Interactions in Conjugates and DNA Duplexes.Molecules (Basel, Switzerland) · 2024Article
- Engineering Central Substitutions in Heptamethine Dyes for Improved Fluorophore Performance.JACS Au · 2024Article
- Mechanistic Insight into the Thermal "Blueing" of Cyanine Dyes.Journal of the American Chemical Society · 2024Article
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Authors and funding
5 authors.
Funding
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Abstract
Cyanine dyes are a class of organic, usually cationic molecules containing two nitrogen centers linked through conjugated polymethine chains. The synthesis and reactivity of cyanine derivatives have been extensively investigated for decades. Unlike the recently described phototruncation process, the thermal truncation (chain shortening) reaction is a phenomenon that has rarely been reported for these important fluorophores. Here, we present a systematic investigation of the truncation of heptamethine cyanines (Cy7) to pentamethine (Cy5) and trimethine (Cy3) cyanines via homogeneous, acid-base-catalyzed nucleophilic exchange reactions. We demonstrate how different substituents at the C3' and C4' positions of the chain and different heterocyclic end groups, the presence of bases, nucleophiles, and oxygen, solvent properties, and temperature affect the truncation process. The mechanism of chain shortening, studied by various analytical and spectroscopic techniques, was verified by extensive
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