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

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.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0028-340E-2 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0029-1EC2-5
Genre: Journal Article

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 Creators:
Kolmakov, K.1, Author              
Hebisch, E.1, Author              
Wolfram, T., Author
Nordwig, L.1, Author              
Wurm, C. A.1, Author              
Ta, H.1, Author              
Westphal, V.1, Author              
Belov, V. N.1, Author              
Hell, S. W.1, Author              
Affiliations:
1Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society, ou_578627              

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Free keywords: dyes/pigments;fluorescence;structure–activity relationships;super-resolution microscopy;synthesis design
 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.

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Language(s): eng - English
 Dates: 2015-08-132015-09-14
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1002/chem.201501394
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Title: Chemistry-A European Journal
Source Genre: Journal
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Pages: - Volume / Issue: 21 (38) Sequence Number: - Start / End Page: 13344 - 13356 Identifier: -