Asymmetric meso-CF3-BODIPY dyes based on cycloalkanopyrroles

Substituent Effects in Six(Anilido)‐Five(Thiazole) Membered Ring Boron Difluoride Dyes

“…The 11 B chemical shifts appeared in the range of À 1.5-0 ppm, which was more upfield than that of 2-(2'-hydroxyphenyl)benzoxazole borate complexes and anilido-benzoxazole boron difluorides, [35,36] indicating that the boron in BFs derivatives was more shielded than the complexes mentioned above. In addition, the split of 11 B NMR spectra was triplet with coupling constant of 1 J B-F = 26.9-30.3 Hz, which was smaller than the one in BODIPY (33 Hz), but much larger than Boranil dyes (16 Hz) and a little larger compared to the anilidobenzoxazole boron difluorides (22.4-27.2 Hz). In addition to 11 B, 19 F NMR spectra were also recorded.…”

“…In addition, the split of 11 B NMR spectra was triplet with coupling constant of 1 J B-F = 26.9-30.3 Hz, which was smaller than the one in BODIPY (33 Hz), but much larger than Boranil dyes (16 Hz) and a little larger compared to the anilidobenzoxazole boron difluorides (22.4-27.2 Hz). In addition to 11 B, 19 F NMR spectra were also recorded. The resonances displayed at À 130 to À 135 ppm as triplet or broad signal with coupling constant of 1 J F-B = 32.7 to 41.2 Hz.…”

“…Flash column chromatography was performed on silica gel (Merck 7736 Kieselgel 60H). 1 H, 13 C, 11 B and 19 F NMR spectra were recorded on Varian Unity 400 or Agilent Technologies DD2 600 MHz spectrometers. Chemical shifts are reported in δ (ppm) relative to an internal standard.…”

“…Similar to numerous porphyrins, BODIPY derivatives have been used in the application of solar cells and optoelectronic materials. [2,3] From the synthetic chemistry point of view, the skeleton of BODIPY has been further developed from the early symmetric structure to various asymmetric types of ligands anchoring on the À BF 2 moiety [4][5][6][7][8][9][10][11] or even À BR 2 groups, where the fluoride was replaced by other groups such as phenyl, À OCH 3 and others. [12][13][14][15][16] This asymmetric extension lies in several incentives.…”

Contributing to Biochemistry and Optoelectronics: Pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and Cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles via [3+2] Annulation of Acylethynylcycloalka[b]pyrroles with Δ1-Pyrrolines

“…Starting acylethynyltetrahydroindole 1a , b and acylethynyldihydrobenzo[ g ]indole 2 were obtained from corresponding pyrroles and acylbromoacetylenes in the presence of Al 2 O 3 according to published methods [ 24 , 38 ]. 3-(1,4,5,6,7,8-Hexahydrocyclohepta[ b ]pyrrol-2-yl)-1-phenylprop-2-yn-1-one 3 was prepared for the first time from 1,4,5,6,7,8-hexahydrocyclohepta[ b ]pyrrole [ 39 ] and benzoylbromoacetylene.…”