1395897-59-2

Upstream product

• 1269636-16-9 8-(2,6-dichlorophen-1-yl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 108-86-1 bromobenzene 

Downstream Products

• 1395897-71-8 3-phenyl-5-thien-3-yl-8-(2,6-dichlorophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 
• 1395897-72-9 ((C₆H₅)C₉H₄(C₆H₃Cl₂)N₂BF₂)2C₆H₄ 

Relevant academic research and scientific papers

Radical C-H Alkylation of BODIPY Dyes Using Potassium Trifluoroborates or Boronic Acids

A one-step synthetic procedure for the radical C H alkylation of BODIPY dyes has been developed. This new reaction generates alkyl radicals through the oxidation of boronic acids or potassium trifluoroborates and allows the synthesis of mono-, di-, tri-,

Radical C-H Arylation of the BODIPY Core with Aryldiazonium Salts: Synthesis of Highly Fluorescent Red-Shifted Dyes

We describe herein the first radical C-H arylation of BODIPY dyes. This novel, general, one-step synthetic procedure uses ferrocene to generate aryl radical species from aryldiazonium salts and allows the straightforward synthesis of brightly fluorescent (Φ>0.85) 3,5-diarylated and 3-monoarylated boron dipyrrins in up to 86% yield for a broad range of aryl substituents. In this way, new and complex dyes with red-shifted spectra can be easily prepared.

Efficient two-step synthesis of water soluble BODIPY-TREN chemosensors for copper(ii) ions

Two simple fluorescent sensors for Cu(ii) ions were synthesized in two reaction steps, using recently developed C-H functionalization reactions for boron dipyrrins, starting from a standard 8-aryl-BODIPY dye and a tris(2-aminoethyl)amine (TREN) ligand. At pH 5, the resulting BODIPY-TREN conjugates are demonstrated to be promising, highly selective, water soluble, Cu(ii) sensors that can permeate the cell membrane.

Visible-Light Excitation of BODIPYs Enables Self-Promoted Radical Arylation at Their 3,5-Positions with Diazonium Salts

A metal- and additive-free photochemical strategy for the direct arylation of boron dipyrromethene dyes (BODIPYs) at their 3,5-positions is reported. The operationally simple approach occurs under illumination by visible light in the absence of any extern

UV-vis spectroscopy of the coupling products of the palladium-catalyzed C-H arylation of the BODIPY core

The steady-state, UV-vis electronic absorption and fluorescence emission properties of a large set of 3-aryl and 3,5-diaryl substituted difluoroboron dipyrromethene dyes obtained via direct, palladium-catalyzed C-H (het)arylation of the BODIPY core are reported. The spectra display the narrow absorption and fluorescence emission bands and the generally quite small Stokes shifts characteristic of classic difluoroboron dipyrrins. As a function of the solvent, the spectral maxima are located within a very narrow wavelength range and are slightly red-shifted with increasing solvent polarizability, which is shown to be the crucial parameter influencing the wavelength position of the maxima. The extended π-conjugation in the 3,5-diaryl products always leads to bathochromically shifted absorption and emission spectra compared to those of the 3-aryl analogues. The derivative with a 3-mesityl substituent has blue-shifted spectra in comparison to its 3-phenyl substituted analogue, reflecting the diminished π-conjugation in the former due to steric strain. The nature of the meso-aryl has only a small effect on the spectral positions but affects the fluorescence quantum yield Φ. The majority of the dyes have high Φ (>0.85), except the compounds with meso-phenyl and meso-(p-nitrophenyl) substituents. Quantum-chemical calculations were performed to evaluate the differences in spectroscopic properties upon substitution of the BODIPY core and to compare them with the corresponding experimental results.

Direct palladium-catalysed C-H arylation of BODIPY dyes at the 3- and 3,5-positions

A new one-step synthetic method towards 3- and 3,5-arylated BODIPY dyes via palladium-catalysed C-H arylation has been developed and its scope has been investigated.