Mono- and di-(2,3,5,6-tetrafluoro-4-N,N-dimethylaminophenyl) meso-tetraarylporphyrins: Synthesis, spectral, structural and electrochemical studies

Abstract

A new series of mono-/di-aminated meso-tetraarylporphyrins has been synthesized and characterized by conventional spectroscopic methods. Crystal structure analysis shows that interactions involving halogens are the major contributors, and the relative contributions are 56% and 53% respectively for MB2c and MB3c. All the compounds were electrochemically analyzed under different reaction conditions and showed a positive shift in the reduction and oxidation potentials. The HOMO–LUMO energy gap was altered with respect to the nature of the supporting electrolyte and reference electrodes used. The linear behavior of Randles-Sevcik plots indicate that the redox processes are diffusion controlled; the first reduction/oxidation is a reversible one-electron step whereas the second reduction/oxidation is a quasi-reversible one-electron process. Results also reveal that the mono-aminated porphyrins are more electron deficient than non-aminated and di-aminated porphyrins.

Carbazole appendedtrans-dicationic pyridinium porphyrin finds supremacy in DNA binding/photocleavage over a non-carbazolyl analogue

“…† The previously reported metalloporphyrins suggest that the central metal ion, planarity of the complex, and substituents partially affect the HOMO-LUMO gap of porphyrins. 54,[70][71][72] Here, it is evident from the observation that the band gap (ΔE) of carbazole compounds varies highly when compared to that of tetraphenylporphyrin and their Cu(II)/Zn(II) metal complexes, where 2-4 are having the band-gap in the range of 1.68-1.77 eV and MTPPs exhibited in between 2.13-2.20 eV.…”