Fluorescent 1-hydroxy-10-alkylacridin-9(10H)-one BF2-chelates: Large Stokes shift and long emission decay times

• Published in: Dyes and pigments Vol. 184; p. 108816
• Main Authors: Russegger, Andreas, Borisov, Sergey M.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.01.2021
• Subjects: 1-Hydroxyacridones; BF2-fluorophores; Fluorescence; Synthesis; 1-Hydroxyacridones; Fluorescence; Synthesis; BF2-fluorophores
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2020.108816

New 1-hydroxy-10-alkylacridin-9(10H)-one BF2-chelates absorb in the blue-green part of the electromagnetic spectrum and emit fluorescence with moderate quantum yields of 8–45% in toluene. The dyes show large Stokes shifts about 4300 cm−1, decay times between 5 ns and 15 ns in toluene and high photostabilities. Introduction of a fluorine atom into the acridone cycle results in an increase of the fluorescence quantum yield and decay time whereas immobilization in a rigid polymer matrix (polystyrene) further extends the lifetime up to 18 ns. Large Stokes shifts and long emission decay time make this dye class an interesting platform for time-resolved imaging and sensing applications. [Display omitted] •New fluorescent BF2-chelates based on 1-hydroxy acridone are prepared.•The dyes feature large Stokes shifts of about 4300 cm−1 and high photostabilities.•The fluorinated derivative possesses long fluorescence decay time of 15 ns.