Solvent and pH Dependent Fluorescent Properties of a Dimethylaminostyryl Borondipyrromethene Dye in Solution

[en] Steady-state and time-resolved fluorescence techniques have been used to study the photophysical properties of the fluorescent BODIPY-derived dye 3-{2-[4-(dimethylamino)phenyl]ethenyl}-4,4-difluoro-8-(4-methoxyphenyl)-1,5,7-trimethyl-3a,4a-diaza-4-bora-s-indacene. This compound has been synthesized via a microwave-assisted condensation of p-N,N-dimethylaminobenzaldehyde with the appropriate 1,3,5,7-tetramethyl substituted borondipyrromethene unit. The fluorescence properties of the dye are strongly solvent dependent: increasing the solvent polarity leads to lower fluorescence quantum yields and lifetimes, and the wavelength of maximum fluorescence emission shifts to the red. The Catalán solvent scales are found to be the most suitable for describing the solvatochromic shifts of the fluorescence emission. These are dominated by polarity/polarizability effects, as confirmed by quantum-chemical calculations performed in the dielectric continuum approximation. Fluorescence decay profiles of the dye can be described by a single-exponential fit in most solvents investigated, while two decay times are found in alcohols. The dye undergoes a reversible protonation-deprotonation reaction in the acidic pH range with a pKa of 2.25 in acetonitrile solution. Fluorimetric titrations as a function of pH produce fluorescence emission enhancements at lower pH. The fluorescence excitation spectra show a hypsochromic shift from 600 nm for the neutral amine to 553 nm for the ammonium form, so that ratiometric measurements can be used to determine pKa.

Disciplines :

Physics

Author, co-author :

Baruah, M.

Qin, W.

Flors, C.

Hofkens, J.

Vallée, R.A.L.

Beljonne, David ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux

Van Der Auweraer, M.

De Borggraeve, W.M.

Boens, N.

Language :

English

Title :

Solvent and pH Dependent Fluorescent Properties of a Dimethylaminostyryl Borondipyrromethene Dye in Solution

Publication date :

11 May 2006

Journal title :

Journal of Physical Chemistry. A

ISSN :

1089-5639

Publisher :

American Chemical Society, Washington, United States - District of Columbia

Volume :

110

Issue :

1855

Pages :

5998-6009

Peer reviewed :

Peer Reviewed verified by ORBi

Research unit :

S817 - Chimie des matériaux nouveaux

Research institute :

R400 - Institut de Recherche en Science et Ingénierie des Matériaux

Commentary :

Publié en ligne le 20 avril 2006

Available on ORBi UMONS :

since 10 June 2010

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