5,10,15-Triaryltetrabenzocorroles functionalized with different electron-withdrawing groups on the beta,beta'-fused rings have been prepared by a cross-coupling Heck procedure between octabrominated copper corrole and a terminal alkene bearing electron-withdrawing moieties. The spectroscopic characterization of these complexes showed red-shifted UV-vis absorption bands characterized by a significant band broadening. The same feature was observed in the case of NMR spectra, where low-resolution groups of signals were observed. This behavior derives from a strong tendency of these macrocycles to aggregate in solution, as has been demonstrated by an (1)H NMR study performed on one of these tetrabenzocorroles. The influence of the substituents on the fused benzene ring on the properties of the tetrabenzocorroles was investigated by electrochemistry and spectroelectrochemistry, and comparisons were made between properties of the newly synthesized compounds and those of the tetrabenzocorroles reported earlier in the literature.
Pomarico, G., Nardis, S., Stefanelli, M., Cicero, D.o., Vicente, M., Fang, Y., et al. (2013). Synthesis and characterization of functionalized meso-triaryltetrabenzocorroles. INORGANIC CHEMISTRY, 52(15), 8834-8844 [10.1021/ic4010467].
Synthesis and characterization of functionalized meso-triaryltetrabenzocorroles
NARDIS, SARA;STEFANELLI, MANUELA;CICERO, DANIEL OSCAR;PAOLESSE, ROBERTO
2013-01-01
Abstract
5,10,15-Triaryltetrabenzocorroles functionalized with different electron-withdrawing groups on the beta,beta'-fused rings have been prepared by a cross-coupling Heck procedure between octabrominated copper corrole and a terminal alkene bearing electron-withdrawing moieties. The spectroscopic characterization of these complexes showed red-shifted UV-vis absorption bands characterized by a significant band broadening. The same feature was observed in the case of NMR spectra, where low-resolution groups of signals were observed. This behavior derives from a strong tendency of these macrocycles to aggregate in solution, as has been demonstrated by an (1)H NMR study performed on one of these tetrabenzocorroles. The influence of the substituents on the fused benzene ring on the properties of the tetrabenzocorroles was investigated by electrochemistry and spectroelectrochemistry, and comparisons were made between properties of the newly synthesized compounds and those of the tetrabenzocorroles reported earlier in the literature.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
