N‐Methyl‐21‐thiaporphyrins

摘要: We synthesized five N-methyl-meso-tetraaryl-21-thiaporphyrins in 55–60 % yield by treating the appropriate meso-tetraaryl-21-thiaporphyrin with CH3I. The N-methyl-21-thiaporphyrins were characterized HRMS, 1D and 2D NMR spectroscopy, absorption fluorescence electrochemical techniques, structure of one compounds was obtained X-ray crystallography. spectroscopy used to identify all resonances observed 1H spectra N-methyl-21-thiaporphyrins. studies indicated that methylation occurred at pyrrole ring is opposite thiophene ring. In spectra, resulted significant upfield shifts protons; maximum noted for protons N-methylated revealed deviation from reference plane defined four meso carbon atoms, porphyrin strongly distorted compared 21-thiaporphyrin showed Q bands strong Soret band, which bathochromically shifted those 21-thiaporphyrins. on oxidation potentials became less positive there negligible reduction potentials; HOMO–LUMO energy gap decreased are weakly fluorescent low quantum yields singlet-state lifetimes. spectral N-methylation 21-thiaporphyrins significantly alters electronic properties macrocycle.