One-pot synthesis of N-confused porphyrin-dipyrrin conjugates and their optical properties.

Abstract

A conjugated N-confused porphyrin-dipyrrin system NCP-IN-X (X = H, Br, Cl, OMe, COOEt) has been reported via N-Confused tetraphenylporphyrin (NCTPP) as a π-enlarged pyrrole and substituted trimethylindole subunits in 75-82% yields by one pot. All the NCP-INs show red-shifted absorption and emission in the NIR range compared with NCTPP in a series nonpolar and polar solvents. Interesting, relative higher emission in DMF can be observed. The structures of dipyrrin-NCP conjugates are characterized by 1H-NMR and high resolution mass spectrum (HR-MS). Four frontier molecular orbital and simulated stick absorption spectra are calculated by DFT and TD-DFT calculation which is in good agreement with the experiments.