850130-91-5Relevant academic research and scientific papers
Novel BODIPY preparations from sterically hindered pyrroles. Synthesis and photophysical behavior in solution, polystyrene nanoparticles, and solid phase
Meallet-Renault,Clavier,Dumas-Verdes,Badre,Shmidt, E. Yu.,Mikhaleva,Laprent,Pansu,Audebert,Trofimov
body text, p. 2247 - 2256 (2009/04/10)
Trimesityl-BODIPY (TMB), a new derivative of 4,4-difluoro-4-bora-3a,4a- diaza-s-indacene belonging to fluores-cent nanostructures series, was synthesized from the corresponding pyrrole by the Trofimov reaction. This reaction was also employed to obtain 2-[2.2]paracyclophanylpyrrole from 5-acetyl[2.2]-paracyclophane. The spectral properties of TMB have been investigated in dichloromethane, nanolatex (polystyrene) films prepared by rapid solvent evaporation, and microcrystals. Comparative analysis of TMB properties with those of mesityl-BODIPY (MB) was performed. TMB was prepared to minimize π-π interactions in order to preserve luminescence in the aggregate state. Both fluorophores were shown to form fluorescing aggregates in the amorphous state (film). Fluorescence spectra (extinction and lifetime) were also studied. In crystal, MB shows a weaker fluorescence, while TMB behaves as a single fluorescing aggregate with a lifetime of 9.5 ns.
Synthesis of 2-mesityl-3-methylpyrrole via the Trofimov reaction for a new BODIPY with hindered internal rotation
Zaitsev, Alexey B.,Méallet-Renault, Rachel,Schmidt, Elena Yu.,Mikhaleva, Al'bina I.,Badré, Sophie,Dumas, Cécile,Vasil'tsov, Alexander M.,Zorina, Nadezhda V.,Pansu, Robert B.
, p. 2683 - 2688 (2007/10/03)
The reaction of E-ethylmesitylketoxime with acetylene in the system KOH/DMSO (the Trofimov reaction) (70-74°C, 3 h, atmosphere pressure) affords 2-mesityl-3-methylpyrrole (23%), 2-mesityl-3-methyl-1-vinylpyrrole (8%), Z- (5%) and E- (2%) isomers of O-vinylethylmesitylketoxime. Initial ethylmesitylketoxime was prepared in two ways: via very slow oximation of ethylmesitylketone in 30% yield after 8 months, and, more efficiently, by oximation of ethylmesitylketimine hydrochloride derived from bromomesitylene in several steps. 2-Mesityl-3-methylpyrrole was used for the synthesis of 4,4-difluoro-2,6-dimethyl-3,5,8-trimesityl-4-bora-3a,4a-diaza-s-indacene with mesityl substituents having hindered internal rotation and preventing π-stacking at high concentrations. The latter factor enables the fluorescence of crystals of the prepared BODIPY, a feature that was not previously documented for such molecules.
