1308671-68-2Relevant academic research and scientific papers
Synthesis, photophysical, electrochemical, and electrogenerated chemiluminescence studies. multiple sequential electron transfers in BODIPY monomers, dimers, trimers, and polymer
Nepomnyashchii, Alexander B.,Broering, Martin,Ahrens, Johannes,Bard, Allen J.
, p. 8633 - 8645 (2011)
Synthesis of the C8 BODIPY monomers, dimers, and trimers, a C8 polymer, and N8 aza-BODIPY monomer and dimer was carried out. Methyl and mesityl C8-substituted monomers, dimers, and trimers were used. Dimers, trimers, and polymer were formed chemically through the β-β (2/6) positions by oxidative coupling using FeCl3. A red shift of the absorbance and fluorescence is observed with addition of monomer units from monomer to polymer for C8 dyes. The aza-BODIPY dye shows red-shifted absorbance and fluorescence compared with the C8 analogue. Cyclic voltammetry shows one, two, and three one-electron waves on both reduction and oxidation for the monomer, dimer, and trimer, respectively, for the C8 BODIPYs. The separation for the reduction peaks for the C8 dimers is 0.12 V compared with 0.22 V for the oxidation, while the trimers show separations of 0.09 V between reduction peaks and 0.13 V for oxidation peaks. The larger separations between the second and third peaks, 0.25 V for the oxidation and 0.2 V for the reduction, are consistent with a larger energy to remove or add a third electron compared with the second one. The BODIPY polymer shows the presence of many sequential one-electron waves with a small separation. These results provide evidence for significant electronic interactions between different monomer units. The aza-BODIPY dye shows a reduction peak 0.8 V more positive compared to the C8 compound. Aza-BODIPY dimer shows the appearance of four waves in dichloromethane. The separation between two consecutive waves is around 0.12 V for reduction compared with 0.2 V for oxidation, which is comparable with the results for the C 8 dyes. Electrogenerated chemiluminescence (ECL) of the different species was obtained, including weak ECL of the polymer.
