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Volumn 21, Issue 38, 2015, Pages 13344-13356

Far-Red Emitting Fluorescent Dyes for Optical Nanoscopy: Fluorinated Silicon-Rhodamines (SiRF Dyes) and Phosphorylated Oxazines

Author keywords

dyes pigments; fluorescence; structure activity relationships; super resolution microscopy; synthesis design

Indexed keywords

GROUND STATE; OPTICAL RESOLVING POWER; PHOSPHORYLATION; PHOTOBLEACHING; SCAFFOLDS; SILICON; STIMULATED EMISSION; WATER ABSORPTION;

EID: 84940889075     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501394     Document Type: Article
Times cited : (52)

References (92)
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    • for the synthesis and properties of red-emitting rhodamines with extended π-conjugation systems, see
    • for the synthesis and properties of red-emitting rhodamines with extended π-conjugation systems, see:, J. Liu, Z. Diwu, W.-Y. Leung, Y. Lu, B. Patch, R. P. Haugland, Tetrahedron Lett. 2003, 44, 4355-4359.
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    • the structure of a rhodamine dye CFTM680R with absorption and emission maxima at λ=680 and 701 nm, respectively, is unknown; see
    • the structure of a rhodamine dye CFTM680R with absorption and emission maxima at λ=680 and 701 nm, respectively, is unknown; see: www.linaris.de/php/CMS/usercontent/deutsch/PDFs/CF%20dye%20selection%20guide.pdf.
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    • For the properties of ATTO dyes, see: www.atto-tec.com. Other red-emitting dyes include ATTO 655 (oxazine) and (a new one; probably carbopyronine) ATTO 665. Both dyes absorb/emit with maxima at λ=663/684 nm, but the fluorescence quantum yield of the former is 30 %, and of the latter is 60 % (all data were reported for aqueous solutions).
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    • GSDIM: ground-state depletion followed by individual molecular return microscopy was performed by using a Leica SR GSD (3D) microscope. This super-resolution microscopy mode is based on the depletion of the fluorescent ("bright") state of all or nearly all molecules by shelving them in a dark (triplet) state. Subsequently, individual molecules return to the ground state (spontaneously or by triggering with UV light). These single markers have to be located at distances greater that the diffraction limit. They may be detected and localized by using a charge-coupled device (CCD) camera and collecting photons emitted by each of them. All of these events occur within micro- or milliseconds and can be repeated a hundred or thousand times. The acquisition of all of these "frames" enables the whole image to be reconstructed with a localization precision proportional to 1/√N
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    • The instability of rhodamine amides towards alkaline hydrolysis has already been reported, see
    • The instability of rhodamine amides towards alkaline hydrolysis has already been reported, see:, V. P. Boyarskiy, V. N. Belov, R. Medda, B. Hein, M. Bossi, S. W. Hell, Chem. Eur. J. 2008, 14, 1784-1792.
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    • The dye KK114L (previously reported as KK1119; see ref. [5d]) has the same fluorophore as KK114 (see refs. [5d, e], except the linker with a carboxylic acid residue is elongated by one CH2 group. This provides a much more stable NHS ester (see ref. [5c]), although the spectral properties remain exactly the same. Abberior STAR REDis an NHS carbonate with the same fluorophore as that in KK114 (for the structure, see Scheme 1 and ref. [5d]). Under STED conditions, these two rhodamines are more photostable than SiR-CO2H or SiRF dyes, despite having additional conjugated double bonds (as seen in Scheme 1). The latter may undergo photoinduced reactions that cause partial bleaching (so-called "bluing", that is, hypsochromic and hypsofluoric shifts). No less importantly, derivatives of KK114 are far less sensitive to changes in the excitation/depletion conditions and other setup settings and develop far less re-excitation artifacts
    • The dye KK114L (previously reported as KK1119; see ref. [5d]) has the same fluorophore as KK114 (see refs. [5d, e], except the linker with a carboxylic acid residue is elongated by one CH2 group. This provides a much more stable NHS ester (see ref. [5c]), although the spectral properties remain exactly the same. Abberior STAR RED (www.abberior.com) is an NHS carbonate with the same fluorophore as that in KK114 (for the structure, see Scheme 1 and ref. [5d]). Under STED conditions, these two rhodamines are more photostable than SiR-CO2H or SiRF dyes, despite having additional conjugated double bonds (as seen in Scheme 1). The latter may undergo photoinduced reactions that cause partial bleaching (so-called "bluing", that is, hypsochromic and hypsofluoric shifts). No less importantly, derivatives of KK114 are far less sensitive to changes in the excitation/depletion conditions and other setup settings and develop far less re-excitation artifacts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.