A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy
2010 | journal article; research paper. A publication with affiliation to the University of Göttingen.
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A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy
Kolmakov, K. ; Belov, V. N. ; Wurm, C. A. ; Harke, B.; Leutenegger, M. ; Eggeling, C. & Hell, S. (2010)
European Journal of Organic Chemistry, 2010(19) pp. 3593-3610. DOI: https://doi.org/10.1002/ejoc.201000343
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- Authors
- Kolmakov, Kirill ; Belov, Vladimir N. ; Wurm, Christian Andreas ; Harke, Benjamin; Leutenegger, Marcel ; Eggeling, Christian ; Hell, Stefan
- Abstract
- Biological microscopy favors photostable fluorescent markers with large fluorescence quantum yields, low dark triplet state population, good biocompatibility and absorption and emission maxima in the near-infrared, where cellular autofluorescence is minimized. In the present study, carbopyronines absorbing around 640 nm and emitting at around 660 nm, with a low intersystem crossing rate (k(isc) approximate to 0.5 X 10(6) s(-1)) and excellent properties for cellular imaging were synthesized. A general synthetic route to carbopyronines with functional groups variable in the final steps of the synthesis or in the resulting fluorescent dye is presented. Possessing two 2-methoxyethyl groups, the parent dye is soluble in water and most organic solvents. Demethylation of the dye or its precursors is straightforward, clean, and furnishes compounds with one or two 2-hydroxyethyl groups, which can be used for further transformations. Modifications in the linker-containing carboxy group are also possible. A multistep synthesis of the dye starting from a simple precursor and utilizing a single temporary protective group is described. The presented approach may be further applied to the design of caged carbopyronines.
- Issue Date
- 2010
- Journal
- European Journal of Organic Chemistry
- ISSN
- 1434-193X
- Language
- English