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Far-red emitting fluorescent dyes for optical nanoscopy: Fluorinated silicon–rhodamines (SiRF dyes) and phosphorylated oxazines.

MPS-Authors
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Kolmakov,  K.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Hebisch,  E.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Nordwig,  L.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Wurm,  C. A.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Ta,  H.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Westphal,  V.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Belov,  V. N.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Hell,  S. W.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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2180942_Suppl.pdf
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Citation

Kolmakov, K., Hebisch, E., Wolfram, T., Nordwig, L., Wurm, C. A., Ta, H., et al. (2015). Far-red emitting fluorescent dyes for optical nanoscopy: Fluorinated silicon–rhodamines (SiRF dyes) and phosphorylated oxazines. Chemistry-A European Journal, 21(38), 13344-13356. doi:10.1002/chem.201501394.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0028-340E-2
Abstract
Far-red emitting fluorescent dyes for optical microscopy, stimulated emission depletion (STED), and ground-state depletion (GSDIM) super-resolution microscopy are presented. Fluorinated silicon–rhodamines (SiRF dyes) and phosphorylated oxazines have absorption and emission maxima at about λ≈660 and 680 nm, respectively, possess high photostability, and large fluorescence quantum yields in water. A high-yielding synthetic path to introduce three aromatic fluorine atoms and unconventional conjugation/solubilization spacers into the scaffold of a silicon–rhodamine is described. The bathochromic shift in SiRF dyes is achieved without additional fused rings or double bonds. As a result, the molecular size and molecular mass stay quite small (<600 Da). The use of the λ=800 nm STED beam instead of the commonly used one at λ=750–775 nm provides excellent imaging performance and suppresses re-excitation of SiRF and the oxazine dyes. The photophysical properties and immunofluorescence imaging performance of these new far-red emitting dyes (photobleaching, optical resolution, and switch-off behavior) are discussed in detail and compared with those of some well-established fluorophores with similar spectral properties.