Informace o publikaci
C1′-SubstitutedPenta- and Heptamethine Cyanines:Synthetic Scope and Properties
| Autoři | |
|---|---|
| Rok publikování | 2026 |
| Druh | Recenzovaný odborný článek |
| Časopis / Zdroj | Journal of Organic Chemistry |
| Fakulta / Pracoviště MU | |
| Citace | |
| www | https://pubs.acs.org/joceah/article/91/28/9718/5201865/C1-Substituted-Penta-and-Heptamethine-Cyanines |
| Doi | https://doi.org/10.1021/acs.joc.6c00573 |
| Klíčová slova | UNSYMMETRICAL CYANINE DYES; SINGLET OXYGEN; PH; CHAIN; WATER; PHOTOSTABILITY; SUBSTITUENTS; NITROGEN; DESIGN; PROBES |
| Přiložené soubory | |
| Popis | Cyanine dyes are of particular importance in contemporary bioimaging and fluorescence-based applications. The structure of these dyes features a polymethine linker, which exerts a substantial influence on their spectroscopic properties. Despite the extensive use of cyanines, synthetic methods for the functionalization of their polymethine chain remain limited. This study presents a comprehensive methodology for the synthesis of penta- and heptamethine cyanines bearing diverse substituents in the C1 ' (chain) position. It is a follow-up to our recent report (), which explained why cyanines with bulky and electron-withdrawing groups in this position exhibit significantly altered absorption properties. The synthetic protocol demonstrates a high functional-group tolerance, moderate to excellent yields, and flexibility toward the reaction partners, thus establishing itself as a valuable tool for the preparation of new cyanine dyes. The steady-state absorption and emission spectra, singlet-oxygen production and photooxygenation efficiencies, and photostabilities of the synthesized derivatives are presented herein. Furthermore, our results indicate that the selected cyanines exhibit a high degree of sensitivity to pH variations and to nucleophilic addition, thus illustrating the potential of the novel cyanine derivatives to serve as sensors and probes in a variety of biological applications. |
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