1395897-65-0

Basic information

• Product Name: 3-phenyl-8-(p-nitrophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• Synonyms: 3-phenyl-8-(p-nitrophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• CAS NO: 1395897-65-0
• Molecular Weight: 389.169
• Mol File: 1395897-65-0.mol

Chemical Properties

• CAS DataBase Reference: 3-phenyl-8-(p-nitrophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-8-(p-nitrophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene(1395897-65-0)
• EPA Substance Registry System: 3-phenyl-8-(p-nitrophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene(1395897-65-0)

Safety Data

• Hazardous Substances Data: 1395897-65-0(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 940903-05-9 10-(4-nitrophenyl)-5,5-difluoro-5H-dipyrrolo[1,2-c:1’,2’-f][1,3,2]diaza-borinin-4-ium-5-uide 

Relevant articles and documents

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.

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.