154793-50-7

Basic information

• Product Name: 1,3,5,7-tetraphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• Synonyms: 1,3,5,7-tetraphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• CAS NO: 154793-50-7
• Molecular Weight: 496.367
• Mol File: 154793-50-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,3,5,7-tetraphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5,7-tetraphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene(154793-50-7)
• EPA Substance Registry System: 1,3,5,7-tetraphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene(154793-50-7)

Safety Data

• Hazardous Substances Data: 154793-50-7(Hazardous Substances Data)

Upstream product

• 94-41-7 benzalacetophenone 
• 13401-33-7 2-[(3,5-diphenyl-2H-pyrrol-2-ylidene)methyl]-3,5-diphenyl-1H-pyrrole 
• 109-63-7 boron trifluoride diethyl etherate 
• 3274-56-4 2,4-diphenylpyrrole 
• 40872-77-3 3,5-diphenyl-1H-pyrrole-2-carbaldehyde 

Relevant articles and documents

A new synthesis of symmetric boraindacene (BODIPY) dyes

BODIPY dyes were synthesized from pyrrole-2-carbaldehyde derivatives in high yields; this constitutes a new approach to this dye framework. The Royal Society of Chemistry.

Effect of Alkyl, Aryl, and meso-Aza Substitution on the Thermal Stability of BODIPY

The effect of peripheral alkyl, aryl, and meso-aza substitution on the thermal stability of BODIPYs in an argon or oxygen atmosphere has been analyzed using thermogravimetric study results. It has been shown that an increase in the length of 2,6-alkyl substituents to seven carbon atoms is accompanied by the growth of BODIPY thermal stability by 80°C. The greatest increase in the destruction temperature of BODIPY (by 100°C) is attained via the introduction of phenyl groups in the 1,3,5,7-positions of its dipyrromethenmethene framework. meso-Aza substitution does not almost produce any effect on the thermal stability of BODIPY dyes. The BODIPY destruction beginning temperature decreases by 60–90°C in the presence of air oxygen. The thermal stability of BODIPY tends to decrease with reducing degree and symmetry of alkyl substitution in the dipyrromethene framework. A lower thermal stability of BODIPY in comparison with zinc(II) dipyrromethenates is due to the participation of fluorine atoms in intramolecular redox processes.

The computational and experimental investigations of photophysical and spectroscopic properties of BF2 dipyrromethene complexes

The electronic excited states of BF2 dipyrromethene (2BrDPM, DPMI, DPMII, PM567 and 4PhDPM) complexes were investigated using the extended multi-configuration quasi-degenerate at the second order of perturbation theory (XMCQDPT2) and the second-order approximate coupled-cluster (CC2) methods. The excitation energies calculated by CC2 are significantly overestimated by 0.42-0.59 eV because of the substantial contributions of double excitation levels to excited states (>10%). However, the calculated XMCQDPT2 excitation energies agree well with experimental ones within the accuracy 0.11-0.20 eV. The very low lasing efficiency (7.8-8.4%) of 4PhDPM compound was explained by the T1 → T4 and T1 → T5 reabsorptions at XMCQDPT2 level of theory. The molecular photonics of pyrromethenes are studied using a combination of the first-principle and semi-empirical calculations. The main mechanism for the deactivation of the energy of the first singlet excited electronic state is the radiative electronic transition for DPMI, DPMII, PM567 and 4PhDPM compounds. Also, the main mechanism for the quenching of fluorescence in considered complexes (except DPMII compound) is the internal conversion. The processes of the internal conversion and intersystem crossing compete with each other in DPMII compound. The measured and calculated fluorescence quantum yields agree well for all considered molecules.