Functionalization of Fluorescent BODIPY Dyes by Nucleophilic Substitution

Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.
Chemical Communications (Impact Factor: 6.83). 02/2006; 42(3):266-8. DOI: 10.1039/b512756d
Source: PubMed


The BODIPY chromophore can be easily modified by nucleophilic mono- or disubstitution of 3,5-dichloroBODIPY with O-, N-, S- and C-nucleophiles. Absorption and fluorescence spectral data of the new BODIPY derivatives are also reported.

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Available from: Wenwu Qin, Feb 27, 2014
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    • "Br − , I − , OAc − , NO 3 − , HSO 4 − , H 2 PO 4 − , and CN − ) were purchased from Aldrich. 3,5-Dichloro-8- (4-tolyl)BODIPY was synthesized according to previously reported methods [8] "
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    ABSTRACT: A novel BODIPY-based colorimetric and fluorescent sensor with an attached urea group (S1) has been synthesized and characterized by FTIR, NMR, and MS analyses. S1 shows high selectivity and sensitivity toward F− ions among several tested anions (Cl−, Br−, I−, OAc−, NO3−, HSO4−, H2PO4−, CN−) in CHCl3. Upon addition of F− ions, the maximum absorption band of S1 in CHCl3 displayed a red shift from 581 to 588 nm. This shift was visually manifested as a color change from pink to blue. When excited at 550 nm, the fluorescent emission intensity of S1 at 608 nm was quenched to over 87% of its initial value. Both a Job's plot and 1H NMR spectra analysis revealed a 1:1 stoichiometric relationship between S1 and the added F− ions. Moreover, we found that the absorption and fluorescence of the S1-F− complex was reversible upon addition of HSO4− ions. Finally, by using F− and HSO4− ions as chemical inputs and the absorbance and fluorescence intensity as outputs, a complementary INHIBIT/IMPLICATION (INH/IMP) logic gate was constructed at the nanoscale level.
    Sensors and Actuators B Chemical 03/2015; 208:538-545. DOI:10.1016/j.snb.2014.11.094 · 4.10 Impact Factor
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    • "Substitution changes the photophysical properties of these dyes dramatically, depending on structure of a substitute, substitution pattern and type of group in meso-position. Some works illustrate it clearly [13] [14] [15]. Furthermore, self-aggregation of BODIPY dyes is insignificant compared with rhodamine-6G, for example, which is another advantage. "
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    ABSTRACT: Emission spectra of diiodine-substituted boron dipyrromethene (I2BODIPY) dye in ethanol solutions and in methylcellulose matrix were studied. The solid patterns were photoexcited at 520 nm and display room temperature phosphorescence with a maximum at 790 nm that is quenched by molecular oxygen at room temperature. Novel sensing material for oxygen concentration detection from 0% to 100% has been developed on the basis of I2BODIPY with 17-fold sensitivity (I-Ar/I-O2), reverse, fast response (1 s) and linear calibration. The sensitivity dependence on the active substance concentration in matrix was shown.
    Sensors and Actuators B Chemical 07/2014; 197:206–210. DOI:10.1016/j.snb.2014.02.085 · 4.10 Impact Factor

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