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Issue 7, 2009
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Photophysics and stability of cyano-substituted boradiazaindacenedyes

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The solvatochromic photophysical properties of two fluorescent, cyano-substituted BODIPY dyes8-(4-bromophenyl)-3,4,4,5-tetracyano-4-bora-3a,4a-diaza-s-indacene (4CN) and 8-(4-bromophenyl)-3,5-dicyano-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (2CN)—have been studied in various solvents by UV–vis spectrophotometry and steady-state and time-resolved fluorometry. These two BODIPY analogues have comparable photophysical properties, implying that displacement of F by CN at boron has a negligible effect. Both compounds have high fluorescence quantum yields Φf (0.65–0.90 for 4CN and 0.63–0.88 for 2CN) in the solvents studied and display mono-exponential fluorescence decay profiles in nonprotic solvents. A new, generalized treatment of the solvent effect based on four mutually independent, empirical solvent scales (dipolarity, polarizability, acidity, and basicity of the medium) indicates that solvent polarizability and, to a lesser degree, solvent (di)polarity are crucial factors causing the solvent-dependent shifts of the UV–vis absorption and fluorescence emission. The rate constants of radiative deactivation (kf) are nearly independent of the nonprotic solvent [kf = (1.4 ± 0.1) × 108 s−1 for 4CN and (1.5 ± 0.2) × 108 s−1 for 2CN]. Both compounds undergo a color change in polar aprotic solvents (acetone, acetonitrile, and N,N-dimethylformamide), which can be stopped by addition of HClO4. The kinetics of this color change indicates that the decomposition of these cyano-substituted BODIPY compounds is complex.

Graphical abstract: Photophysics and stability of cyano-substituted boradiazaindacene dyes

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Supplementary files

Article information

12 Mar 2009
27 Apr 2009
First published
12 May 2009

Photochem. Photobiol. Sci., 2009,8, 1006-1015
Article type

Photophysics and stability of cyano-substituted boradiazaindacene dyes

K. Cieślik-Boczula, K. Burgess, L. Li, B. Nguyen, L. Pandey, W. M. De Borggraeve, M. Van der Auweraer and N. Boens, Photochem. Photobiol. Sci., 2009, 8, 1006
DOI: 10.1039/B905054J

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