1446281-33-9

Upstream product

• 517-22-6 2,4-dimethyl-3-ethyl-pyrrole 
• 619-66-9 4-Carboxybenzaldehyde 
• 7637-07-2 boron trifluoride 
• 1033273-62-9 4,4-difluoro-8-(4-carboxyphenyl)-1,3,5,7-tetramethyl-2,6-diethyl-4-boron-3a,4a-diaza-s-indacene 
• 2450-71-7 Propargylamine 
• 1218921-99-3 4,4-difluoro-8-(4-((succinimid-N-yl)oxycarbonyl)phenyl)-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene 

Downstream Products

• 1446281-35-1 8-(4-(benzamido)methyl-1-benzyl-1H-1,2,3-triazole)-2,8-diethyl-1,3,7,9-tetramethyl-BODIPY 
• 1586046-70-9 C₇₆H₇₁BF₂GaN₁₁O 

Relevant academic research and scientific papers

Near-Infrared-Emitting BODIPY-trisDOTA111In as a Monomolecular Multifunctional Imaging Probe: From Synthesis to In Vivo Investigations

A new generation of monomolecular imaging probes (MOMIP) based on a distyryl-BODIPY (BODIPY=boron-dipyrromethene) coupled with three DOTA macrocycles has been prepared (DOTA=1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid). The MOMIP presents good fluorescence properties and is very stable in serum. The bimodal probe was conjugated to trastuzumab, and an optical in vivo study showed high accumulation of the imaging agent at the tumor site.111In radiometallation of the bioconjugate was performed in high radiochemical yield, highlighting the potential of this new BODIPY-chelators derivative as a bimodal imaging probe.

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 (650-900 nm), suitable for in vivo imaging, making these compounds promising precursors for PET/optical dual-modality imaging agents.

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 Foerster resonance energy transfer (FRET).

Photocatalytic conversion of CO2 to CO using rhenium bipyridine platforms containing ancillary phenyl or BODIPY moieties

Harnessing of solar energy to drive the reduction of carbon dioxide to fuels requires the development of efficient catalysts that absorb sunlight. In this work, we detail the synthesis, electrochemistry, and photophysical properties of a set of homologous fac-ReI(CO)3 complexes containing either an ancillary phenyl (8) or BODIPY (12) substituent. These studies demonstrate that both the electronic properties of the rhenium center and BODIPY chromophore are maintained for these complexes. Photolysis studies demonstrate that both assemblies 8 and 12 are competent catalysts for the photochemical reduction of CO2 to CO in dimethylformamide (DMF) using triethanolamine (TEOA) as a sacrificial reductant. Both compounds 8 and 12 display turnover frequencies (TOFs) for photocatalytic CO production upon irradiation with light (λex ≥ 400 nm) of ～5 h -1 with turnover number (TON) values of approximately 20. Although structural and photophysical measurements demonstrate that electronic coupling between the BODIPY and fac-ReI(CO)3 units is limited for complex 12, this work clearly shows that the photoactive BODIPY moiety is tolerated during catalysis and does not interfere with the observed photochemistry. When taken together, these results provide a clear roadmap for the development of advanced rhenium bipyridine complexes bearing ancillary BODIPY groups for the efficient photocatalytic reduction of CO2 using visible light.