Zitieren Sie bitte immer diesen URN: urn:nbn:de:kobv:b43-456361
Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril
- We introduce herein boron-dipyrromethene (BODIPY) dyes as a new class of fluorophores for the design of reporter dyes for supramolecular host–guest complex formation with cucurbit[7]uril (CB7). The BODIPYs contain a protonatable aniline nitrogen in the meso-position of the BODIPY chromophore, which was functionalized with known binding motifs for CB7. The unprotonated dyes show low fluorescence due to photoinduced electron transfer (PET), whereas the protonated dyes are highly fluorescent. Encapsulation of the binding motif inside CB7 positions the aniline nitrogen at the carbonyl rim of CB7, which affects the pKa value, and leads to a host-induced protonation and thus to a fluorescence increase. The possibility to tune binding affinities and pKa values is demonstrated and it is shown that, in combination with the beneficial photophysical properties of BODIPYs, several new applications of host–dye reporter pairs can be implemented. This includes indicator displacement assays withWe introduce herein boron-dipyrromethene (BODIPY) dyes as a new class of fluorophores for the design of reporter dyes for supramolecular host–guest complex formation with cucurbit[7]uril (CB7). The BODIPYs contain a protonatable aniline nitrogen in the meso-position of the BODIPY chromophore, which was functionalized with known binding motifs for CB7. The unprotonated dyes show low fluorescence due to photoinduced electron transfer (PET), whereas the protonated dyes are highly fluorescent. Encapsulation of the binding motif inside CB7 positions the aniline nitrogen at the carbonyl rim of CB7, which affects the pKa value, and leads to a host-induced protonation and thus to a fluorescence increase. The possibility to tune binding affinities and pKa values is demonstrated and it is shown that, in combination with the beneficial photophysical properties of BODIPYs, several new applications of host–dye reporter pairs can be implemented. This includes indicator displacement assays with favourable absorption and emission wavelengths in the visible spectral region, fluorescence correlation spectroscopy, and noncovalent surface functionalization with fluorophores.…
Autor*innen: | M. A. Alnajjar, Jürgen Bartelmeß, R. Hein, Pichandi Ashokkumar, M. Nilam, W. M. Nau, Knut RurackORCiD, A. Hennig |
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Dokumenttyp: | Zeitschriftenartikel |
Veröffentlichungsform: | Verlagsliteratur |
Sprache: | Englisch |
Titel des übergeordneten Werkes (Englisch): | Beilstein Journal of Organic Chemistry |
Jahr der Erstveröffentlichung: | 2018 |
Organisationseinheit der BAM: | 1 Analytische Chemie; Referenzmaterialien |
1 Analytische Chemie; Referenzmaterialien / 1.9 Chemische und optische Sensorik | |
Veröffentlichende Institution: | Bundesanstalt für Materialforschung und -prüfung (BAM) |
Verlag: | Beilstein-Institut |
Verlagsort: | Frankfurt a. M. |
Jahrgang/Band: | 14 |
Erste Seite: | 1961 |
Letzte Seite: | 1971 |
DDC-Klassifikation: | Naturwissenschaften und Mathematik / Chemie / Analytische Chemie |
Freie Schlagwörter: | BODIPY; Cucurbituril; Fluorescence; PH; Photoinduced Electron Transfer; Supramolecular Chemistry |
Themenfelder/Aktivitätsfelder der BAM: | Umwelt |
Umwelt / Sensorik | |
DOI: | 10.3762/bjoc.14.171 |
URN: | urn:nbn:de:kobv:b43-456361 |
URL: | https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-14-171.pdf |
ISSN: | 1860-5397 |
Verfügbarkeit des Dokuments: | Datei für die Öffentlichkeit verfügbar ("Open Access") |
Lizenz (Deutsch): | Creative Commons - CC BY - Namensnennung 4.0 International |
Datum der Freischaltung: | 06.08.2018 |
Referierte Publikation: | Ja |
Datum der Eintragung als referierte Publikation: | 09.08.2018 |
Schriftenreihen ohne Nummerierung: | Wissenschaftliche Artikel der BAM |