Charged And Confused: Meso-Tetrakis(P-Methoxycarbonyl-Phenyl) N-Confused Porphyrin As A Precursor To Water Soluble Variants

A metal-free meso-tetrakis(p-methoxycarbonylphenyl) N-confused porphyrin (1) was prepared as the precursor for water-soluble derivatives by the reaction between pyrrole, methyl-4-formylbenzoate, and MSA. Tautomeric behavior of the porphyrin 1 in polar and non-polar solvents was probed by H-1 NMR, UV-vis, MCD, steady-state fluorescence, and high-resolution ESI methods and was found to be similar to the previously reported metal-free N-confused porphyrins. The electronic structure and the nature of the excited states in 1 were correlated with the results obtained by density functional theory (DFT) and time-dependent DFT (TDDFT) calculations.