Synthesis and photophysical properties of novel oxadiazole substituted BODIPY fluorophores

Abstract

Using 3-phenyl-5-(5-phenyl-1H-pyrrol-3-yl)-1,2,4-oxadiazole, BODIPYs with the oxadiazole groups at 1,7-positions were prepared and their photophysical properties were characterized. The method employs 2,4-disubstituted pyrrole and various aromatic aldehydes under solvent-free conditions. Due...

1,7‐isoxazolyl Substituted BODIPY Dyes – Synthesis and Photophysical Properties

“…We also noted that, as in the case of 1,7‐aroyl‐ and 1,7‐oxadiazolyl substituted BODIPYs, the largest shift to the red‐light region was obtained for ortho ‐Br 6 d (max λ em =625 nm). Comparing the obtained results of excitation and emission in a series of aroyl‐, [13a] oxadiazolyl‐ [13b] and isoxazolyl substituted BODIPYs obtained by our group, we see that the presence of oxadiazole groups at 1,7‐positions shifts the absorption and emission bands most strongly to the red region of light (Figure 4).…”

“…We chose tert‐ butyl 3‐(4‐chlorophenyl)‐5‐(5‐phenyl‐1 H ‐pyrrol‐3‐yl)isoxazole‐4‐carboxylate 2 with free α ‐position and unsubstituted benzaldehyde 5 a as model reactants for optimization studies. We have tested the first stage of the sequential synthesis of boron‐dipyrromethenes under similar conditions for the synthesis of 1,7‐oxadiazolyl substituted BODIPYs – 120 °C in the absence of a solvent [13b] . However, the formation of a multicomponent mixture was observed, the chromatographic separation of which did not lead to the isolation of the target product (Scheme 2).…”

Synthesis and photophysical properties of 1,7-aroyl BODIPYs: an experimental and theoretical study

“…S1, ESI †). 12 Comparing the excitation and emission values of BODIPYs with various substituents at positions 1,3,5,7, we can conclude that the presence of acceptor groups at positions 1 and 7 shifts the excitation and emission bands to the red light region.…”

“…The synthetic procedure and results of photophysical experiments of 1,7-oxadiazole substituted BODIPY fluorophores were presented in our previous work. 12 The present work is devoted to the synthesis and analysis of the photophysical properties of BODIPYs containing an aroyl fragment at positions 1 and 7 (Scheme 1).…”