Influence of the meso-substituent on strongly red emitting phenanthrene-fused boron–dipyrromethene (BODIPY) fluorophores with a propeller-like conformation

  • Highly emissive phenanthrene-fused boron–dipyrromethene (PBDP) dyes have been spectroscopically characterized in a series of solvents. The influence of different substituents (-H, -I, -CN, -DMA or a 15C5-crown ether) in the para-position of a phenyl ring attached to the meso-position of the BODIPY core is discussed. This family of dyes has an intense emission at lambda > 630 nm, with fluorescence quantum yields between 0.7 and 1.0 in all solvents studied, except in the case of the dimethylamino-substituted derivative, PBDP-DMA, which undergoes excited-state intramolecular charge transfer (CT), leading to broadband dual fluorescence in highly polar solvents. Introduction of a weaker electron donor such as a benzocrown to the meso-position is not able to trigger a second (charge or electron transfer) process and, interestingly, heavy atom (iodine, PBDP-I derivative) substitution at that moiety does also not have a relevant influence on the photophysics, i.e., enhanced intersystemHighly emissive phenanthrene-fused boron–dipyrromethene (PBDP) dyes have been spectroscopically characterized in a series of solvents. The influence of different substituents (-H, -I, -CN, -DMA or a 15C5-crown ether) in the para-position of a phenyl ring attached to the meso-position of the BODIPY core is discussed. This family of dyes has an intense emission at lambda > 630 nm, with fluorescence quantum yields between 0.7 and 1.0 in all solvents studied, except in the case of the dimethylamino-substituted derivative, PBDP-DMA, which undergoes excited-state intramolecular charge transfer (CT), leading to broadband dual fluorescence in highly polar solvents. Introduction of a weaker electron donor such as a benzocrown to the meso-position is not able to trigger a second (charge or electron transfer) process and, interestingly, heavy atom (iodine, PBDP-I derivative) substitution at that moiety does also not have a relevant influence on the photophysics, i.e., enhanced intersystem crossing was not observed. Electrochemical studies of PBDP-DMA complement the data reported and stress the fact that the decrease in fluorescence of PBDP-DMA in highly polar solvents is due to an excited-state CT process rather than to a photoinduced electron transfer (PET).zeige mehrzeige weniger

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Metadaten
Autor*innen:Ana B. Descalzo, H.-J. Xu, Z. Shen, Knut RurackORCiD
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):Journal of Photochemistry and Photobiology A: Chemistry
Jahr der Erstveröffentlichung:2018
Organisationseinheit der BAM:1 Analytische Chemie; Referenzmaterialien
1 Analytische Chemie; Referenzmaterialien / 1.9 Chemische und optische Sensorik
Verlag:Elsevier
Verlagsort:Amsterdam
Jahrgang/Band:352
Erste Seite:98
Letzte Seite:105
DDC-Klassifikation:Naturwissenschaften und Mathematik / Chemie / Analytische Chemie
Freie Schlagwörter:BODIPY dyes; Charge transfer; Fluorescence; Ring fusion
Themenfelder/Aktivitätsfelder der BAM:Umwelt
Umwelt / Sensorik
DOI:10.1016/j.jphotochem.2017.10.034
ISSN:1010-6030
Verfügbarkeit des Dokuments:Datei im Netzwerk der BAM verfügbar ("Closed Access")
Datum der Freischaltung:24.11.2017
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:04.01.2018
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