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On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated BoronDipyrromethene (BODIPY) Dyes in Aqueous Solution

  • The tendency of boron-dipyrromethene (BODIPY) dyes to associate in water is well known, and usually a cause for inferior fluorescence properties. Synthetic efforts to chemically improve BODIPYs’ water solubility and minimize this problem have been numerous in the past. However, a deeper understanding of the phenomena responsible for fluorescence quenching is still required. Commonly, the spectroscopic behaviour in aqueous media has been attributed to aggregate or excimer formation, with such works often centring on a single BODIPY family. Herein, we provide an integrating discussion including very diverse types of BODIPY dyes. Our studies revealed that even subtle structural changes can distinctly affect the association behaviour of the fluorophores in water, involving different photophysical processes. The palette of behaviour found ranges from unperturbed emission, to the formation of H or J aggregates and excimers, to the involvement of tightly bound, preformed excimers. TheseThe tendency of boron-dipyrromethene (BODIPY) dyes to associate in water is well known, and usually a cause for inferior fluorescence properties. Synthetic efforts to chemically improve BODIPYs’ water solubility and minimize this problem have been numerous in the past. However, a deeper understanding of the phenomena responsible for fluorescence quenching is still required. Commonly, the spectroscopic behaviour in aqueous media has been attributed to aggregate or excimer formation, with such works often centring on a single BODIPY family. Herein, we provide an integrating discussion including very diverse types of BODIPY dyes. Our studies revealed that even subtle structural changes can distinctly affect the association behaviour of the fluorophores in water, involving different photophysical processes. The palette of behaviour found ranges from unperturbed emission, to the formation of H or J aggregates and excimers, to the involvement of tightly bound, preformed excimers. These results are a first step to a more generalized understanding of spectroscopic properties vs. structure, facilitating future molecular design of BODIPYs, especially as probes for biological applications.zeige mehrzeige weniger

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Metadaten
Autor*innen:Ana B. Descalzo, Pichandi Ashokkumar, Z. Shen, Knut RurackORCiD
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):ChemPhotoChem
Jahr der Erstveröffentlichung:2019
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:WILEY-VCH
Verlagsort:Weinheim
Jahrgang/Band:4
Ausgabe/Heft:2
Erste Seite:120
Letzte Seite:131
DDC-Klassifikation:Naturwissenschaften und Mathematik / Chemie / Analytische Chemie
Freie Schlagwörter:Aggregates; BODIPY; Excimers; Fluorescence; Photophysics
Themenfelder/Aktivitätsfelder der BAM:Umwelt
Umwelt / Sensorik
DOI:10.1002/cptc.201900235
URN:urn:nbn:de:kobv:b43-497771
ISSN:2367-0932
Verfügbarkeit des Dokuments:Datei für die Öffentlichkeit verfügbar ("Open Access")
Lizenz (Deutsch):License LogoCreative Commons - CC BY - Namensnennung 4.0 International
Datum der Freischaltung:27.11.2019
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:27.11.2019
Schriftenreihen ohne Nummerierung:Wissenschaftliche Artikel der BAM
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