Mono- and Di(dimethylamino)styryl-Substituted Borondipyrromethene and Borondiindomethene Dyes with Intense Near-Infrared Fluorescence
- Four novel borondipyrromethene (BDP) and -diindomethene (BDI) dyes with one or two (dimethylamino)styryl extensions at the chromophore were synthesized and spectroscopically investigated. An X-ray crystal structure shows that the extended auxochrome is virtually planar. All dyes thus display intense red/near infrared (NIR) absorption and emission. The (dimethylamino)styryl group induces a charge-transfer character that entails bright solvatochromic fluorescence, which is only quenched with increasing solvent polarity according to the energy-gap law. The dye with an additional dimethylanilino group at the meso position of BDP shows a remarkable switching of lipophilicity by protonation. Two dyes with an 8-hydroxyquinoline ligand at the meso position display quenched emission in the presence of Hg2+ or Al3+ owing to electron transfer from the excited BDP to the complexed receptor. The BDI dye presents a pH indicator with bright fluorescence and extremely low fluorescence anisotropy.
Autor*innen: | Y.-H. Yu, Ana Belén Descalzo López, Z. Sgen, Holger Röhr, Q. Liu, Y.-W. Wang, Monika Spieles, Y.-Z. Li, Knut RurackORCiD, X.-Z. You |
---|---|
Dokumenttyp: | Zeitschriftenartikel |
Veröffentlichungsform: | Verlagsliteratur |
Sprache: | Englisch |
Titel des übergeordneten Werkes (Englisch): | Chemistry / Asian Journal |
Jahr der Erstveröffentlichung: | 2006 |
Verlag: | Wiley-VCH Verl. |
Verlagsort: | Weinheim |
Jahrgang/Band: | 1 |
Ausgabe/Heft: | 1-2 |
Erste Seite: | 176 |
Letzte Seite: | 187 |
Freie Schlagwörter: | Borondipyrromethene; Dyes; Fluorescence; Indicators; Protonation |
DOI: | 10.1002/asia.200600042 |
ISSN: | 1861-4728 |
ISSN: | 1861-471X |
Verfügbarkeit des Dokuments: | Physisches Exemplar in der Bibliothek der BAM vorhanden ("Hardcopy Access") |
Bibliotheksstandort: | Sonderstandort: Publica-Schrank |
Datum der Freischaltung: | 19.02.2016 |
Referierte Publikation: | Ja |
Datum der Eintragung als referierte Publikation: | 17.07.2006 |