Ratiometric, Fluorescent BODIPY Dye with Aza Crown Ether Functionality: Synthesis, Solvatochromism, and Metal Ion Complex Formation

Qin, W.; Baruah, M.; Sliwa, M.; Van Der Auweraer, M.; De Borggraeve, W.M.; Beljonne, David; Van Averbeke, Bernard; Boens, N.

doi:10.1021/jp800261v

Article (Scientific journals)

Ratiometric, Fluorescent BODIPY Dye with Aza Crown Ether Functionality: Synthesis, Solvatochromism, and Metal Ion Complex Formation

Qin, W.; Baruah, M.; Sliwa, M. et al.

2008 • In Journal of Physical Chemistry. A, 112 (27), p. 6104-6114

Peer Reviewed verified by ORBi

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https://hdl.handle.net/20.500.12907/36288

DOI
10.1021/jp800261v

PubMed
18547040

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Abstract :

[en] A new pH and metal ion-responsive BODIPY-based fluorescent probe with an aza crown ether subunit has been synthesized via condensation of 4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-benzaldehyde with the appropriate 1,3,5,7-tetramethyl substituted boron dipyrromethene moiety. Steady-state and time-resolved fluorometries have been used to study the spectroscopic and photophysical characteristics of this probe in various solvents. 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 Cataln solvent scales are found to be the most suitable for describing the solvatochromic shifts of the fluorescence emission. Fluorescence decay profiles of the dye can be described by a single-exponential fit in nonprotic solvents, whereas two decay times are found in alcohols. Protonation as well as complex formation with several metal ions are investigated in acetonitrile as solvent via fluorometric titrations. The aza crown ether dye undergoes a reversible (de)protonation reaction (p K a = 0.09) and shows a 50 nm blue shift in the excitation spectra and a 10-fold fluorescence increase upon protonation. The compound also forms 1:1 complexes with several metal ions (Li +, Na +, Mg 2+, Ca 2+, Ba 2+, Zn 2+), producing large blue shifts in the excitation spectra and significant cation-induced fluorescence amplifications.

Disciplines :

Physics

Author, co-author :

Qin, W.

Baruah, M.

Sliwa, M.

Van Der Auweraer, M.

De Borggraeve, W.M.

Beljonne, David ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux

Van Averbeke, Bernard

Boens, N.

Language :

English

Title :

Ratiometric, Fluorescent BODIPY Dye with Aza Crown Ether Functionality: Synthesis, Solvatochromism, and Metal Ion Complex Formation

Publication date :

10 July 2008

Journal title :

Journal of Physical Chemistry. A

ISSN :

1089-5639

Publisher :

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

Volume :

112

Issue :

Pages :

6104-6114

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 le 12 juin 2008

Available on ORBi UMONS :

since 10 June 2010

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