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 :

Physique

Auteur, co-auteur :

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.

Langue du document :

Anglais

Titre :

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

Date de publication/diffusion :

11 mai 2006

Titre du périodique :

Journal of Physical Chemistry. A

ISSN :

1089-5639

Maison d'édition :

American Chemical Society, Washington, Etats-Unis - District de Columbia

Volume/Tome :

110

Fascicule/Saison :

1855

Pagination :

5998-6009

Peer reviewed :

Peer reviewed vérifié par ORBi

Unité de recherche :

S817 - Chimie des matériaux nouveaux

Institut de recherche :

R400 - Institut de Recherche en Science et Ingénierie des Matériaux

Commentaire :

Publié en ligne le 20 avril 2006

Disponible sur ORBi UMONS :

depuis le 10 juin 2010

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citations Scopus^®

228

citations Scopus^®
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210

OpenCitations

201

citations OpenAlex

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