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Synthesis and spectroscopic characterization of fluorophore-labeled oligospiroketal rods

  • Fluorescence probes consisting of well-established fluorophores in combination with rigid molecular rods based on spirane-type structures were investigated with respect to their fluorescence properties under different solvent conditions. The attachment of the dyes was accomplished by 1,3-dipolar cycloaddition between alkynes and azides (click' reaction) and is a prime example for a novel class of sensor constructs. Especially, the attachment of two (different) fluorophores on opposite sides of the molecular rods paves the way to new sensor systems with less bulky (compared to the conventional DNA- or protein-based concepts), nevertheless rigid spacer constructs, e.g., for FRET-based sensing applications. A detailed photophysical characterization was performed in MeOH (and in basic H2O/MeOH mixtures) for i) rod constructs containing carboxyfluorescein, ii) rod constructs containing carboxyrhodamine, iii) rod constructs containing both carboxyfluorescein and carboxyrhodamine, and iv) rod constructs containing both pyrene and peryleneFluorescence probes consisting of well-established fluorophores in combination with rigid molecular rods based on spirane-type structures were investigated with respect to their fluorescence properties under different solvent conditions. The attachment of the dyes was accomplished by 1,3-dipolar cycloaddition between alkynes and azides (click' reaction) and is a prime example for a novel class of sensor constructs. Especially, the attachment of two (different) fluorophores on opposite sides of the molecular rods paves the way to new sensor systems with less bulky (compared to the conventional DNA- or protein-based concepts), nevertheless rigid spacer constructs, e.g., for FRET-based sensing applications. A detailed photophysical characterization was performed in MeOH (and in basic H2O/MeOH mixtures) for i) rod constructs containing carboxyfluorescein, ii) rod constructs containing carboxyrhodamine, iii) rod constructs containing both carboxyfluorescein and carboxyrhodamine, and iv) rod constructs containing both pyrene and perylene parts. For each dye (pair), two rod lengths with different numbers of spirane units were synthesized and investigated. The rod constructs were characterized in ensemble as well as single-molecule fluorescence experiments with respect to i) specific roddye and ii) dyedye interactions. In addition to MeOH and MeOH/NaOH, the rod constructs were also investigated in micellar systems, which were chosen as a simplified model for membranes.zeige mehrzeige weniger

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Metadaten
Verfasserangaben:Anne Techen, Sylvia Czapla, Kristian Möllnitz, Dennis B. BudachGND, Pablo WessigORCiDGND, Michael Uwe KumkeORCiDGND
DOI:https://doi.org/10.1002/hlca.201200616
ISSN:0018-019X
ISSN:1522-2675
Titel des übergeordneten Werks (Englisch):Helvetica chimica acta
Verlag:Wiley-VCH
Verlagsort:Weinheim
Publikationstyp:Wissenschaftlicher Artikel
Sprache:Englisch
Jahr der Erstveröffentlichung:2013
Erscheinungsjahr:2013
Datum der Freischaltung:26.03.2017
Freies Schlagwort / Tag:Carboxyfluorescein; Carboxyrhodamine; Fluorescence; Forster resonance energy transfer (FRET); Molecular rods; Perylene; Pyrene
Band:96
Ausgabe:11
Seitenanzahl:22
Erste Seite:2046
Letzte Seite:2067
Fördernde Institution:Deutsche Forschungsgemeinschaft [We1850-7/1-2]
Organisationseinheiten:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert
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