0000000000647646
AUTHOR
Bertrand Brizet
High Yield SNAr on 8-Halogenophenyl-BODIPY with Cyclic and Acyclic Polyamines
Selective nucleophilic aromatic substitutions with several polyamines were performed in very good yields on halogeno-phenyl BODIPY derivatives containing an activating nitro group.
Boron functionalization of BODIPY by various alcohols and phenols.
The synthesis of new B–O BODIPY derivatives functionalized with different alkoxy or diarylalkoxy derivatives is described. These compounds were synthesized from the reaction of different B–F BODIPY precursors with various alcohols and phenols, in the presence of AlCl3. Water-soluble dyes could be synthesized as well with this method, specifically by the introduction of polyethyleneglycol (PEG) groups. A photophysical study of the different compounds was performed, and showed that the B–O BODIPY derivatives exhibit rich fluorescence properties. Finally, the conjugation of the BODIPY core has been extended using two distyryl groups, hence providing NIR emitting BODIPY derivatives, in which on…
DMAP-BODIPY Alkynes: A Convenient Tool for Labeling Biomolecules for Bimodal PET-Optical Imaging
Several new boron dipyrromethene/N,N-dimethylaminopyridine (BODIPY-DMAP) assemblies were synthesized as precursors for bimodal imaging probes (optical imaging, OI/positron emission tomography, PET). The photophysical properties of the new compounds were also studied. The first proof-of-concept was obtained with the preparation of several new BODIPY-labeled bombesins and evaluation of the affinity for bombesin receptors by using a competition binding assay. Fluorination reactions were investigated on DMAP-BODIPY precursors as well as on DMAP-BODIPY-labeled bombesins. Chemical modifications on the BODIPY core were also performed to obtain luminescent dyes emitting in the therapeutic window (6…
B,B-Diporphyrinbenzyloxy-BODIPY dyes: synthesis and antenna effect.
B,B-Diporphyrinbenzyloxy-BODIPY derivatives have been prepared in high yields, and the photophysical properties are reported. Singlet energy transfers from BODIPY to the porphyrin units have been analyzed.
Synthesis and study of new precursors for bimodal optic/PET or optic/SPECT imaging
This thesis was performed at the Institut de Chimie Moléculaire de d’Université de Bourgogne (France) and in the Département de chimie de l’Université de Sherbrooke (Québec). The aim of this work was to design new BODIPY derivatives in order to obtain optimal properties for in vivo bimodal optical/PET or SPECT imaging. The modifications concern the hydrosolubilisation of these organic dyes, as well as the shifting of the absorption and emission bands toward the therapeutic window, where the light is less attenuated by biological tissues. Solutions allowing the bioconjugation of BODIPY on a bombesin derivative, a peptide which targets receptors surexpressed in tumor cells, were also investig…
ChemInform Abstract: Boron Functionalization of BODIPY by Various Alcohols and Phenols
The synthesis of new B–O BODIPY derivatives functionalized with different alkoxy or diarylalkoxy derivatives is described. These compounds were synthesized from the reaction of different B–F BODIPY precursors with various alcohols and phenols, in the presence of AlCl3. Water-soluble dyes could be synthesized as well with this method, specifically by the introduction of polyethyleneglycol (PEG) groups. A photophysical study of the different compounds was performed, and showed that the B–O BODIPY derivatives exhibit rich fluorescence properties. Finally, the conjugation of the BODIPY core has been extended using two distyryl groups, hence providing NIR emitting BODIPY derivatives, in which on…
BODIPY Dyes Functionalized with Pendant Cyclic and Acyclic Polyamines
The synthesis and characterization of a series of BODIPY derivatives substituted with acyclic and cyclic polyamines, in particular, cyclen and homocyclen, are reported. The 19F NMR, UV/Vis, and fluorescence spectroscopic data of these compounds are discussed. One compound was found to be very selective for CuII ions, which makes it a very promising system for CuII detection.
Origin of the temperature dependence of the rate of singlet energy transfer in a three-component truxene-bridged dyads
We report a truxene-based dyad built upon one donor (tri-meso-phenylzinc(II)porphyrin) and two acceptors (octa-β-alkylporphyrin free base) in which the donor exhibits free rotation around a Ctruxene-Cmeso single bond at 298 K in fluid solution but not at 77 K in a glass matrix, whereas the acceptors have very limited motion as they are blocked by β-methyl groups. This case is interesting because all the structural and spectroscopic parameters affecting the rate for singlet energy transfer according to a Förster Resonance Energy Transfer are only weakly temperature dependent, leaving only the Dexter mechanism explaining the larger variation in rate of energy transfers with the temperature h…
Slow and Fast Singlet Energy Transfers in BODIPY-gallium(III)corrole Dyads Linked by Flexible Chains
Red (no styryl), green (monostyryl), and blue (distyryl) BODIPY-gallium(III) (BODIPY = boron-dipyrromethene) corrole dyads have been prepared in high yields using click chemistry, and their photophysical properties are reported. An original and efficient control of the direction of the singlet energy transfers is reported, going either from BODIPY to the gallium-corrole units or from gallium-corroles to BODIPY, depending upon the nature of the substitution on BODIPY. In one case (green), both directions are possible. The mechanism for the energy transfers is interpreted by means of through-space Förster resonance energy transfer (FRET).
CCDC 984188: Experimental Crystal Structure Determination
Related Article: Bertrand Brizet, Victor Goncalves, Claire Bernhard, Pierre D. Harvey, Franck Denat and Christine Goze|2014|Chem.-Eur.J.|20|12933|doi:10.1002/chem.201402379
CCDC 931678: Experimental Crystal Structure Determination
Related Article: Bertrand Brizet, Claire Bernhard, Yulia Volkova, Yoann Rousselin, Pierre D. Harvey, Christine Goze, Franck Denat|2013|Org.Biomol.Chem.|11|7729|doi:10.1039/C3OB41370E