Synthesis, photoinduced amination and topological indices of novel porphyrin dyads

Muhammad Yaseen, Muhammad A. Rashid, Muhammad A. Iqbal, Zahid Farooq, Muhammad Idrees, Muhammad A. Qayyum, Azeem Intisar, Mian H.R. Mahmood, Ibrahim Khan, Muhammad Latif

Research output: Journal PublicationArticlepeer-review

1 Citation (Scopus)


Transition-metal-catalyzed homo and hetero coupling is a rapidly growing area of research. This work refers to the nickel-catalyzed photoinduced amination study of β-bromotetraarylporphyrin and its Ni(II), Zn(II) and Cu(II) complexes. The selective mono β-bromination of 5,10,15,20-tetrakis(4′-isopropylphenyl)porphyrin was achieved with N-bromosuccinimide. Under similar conditions, β-bromination of Ni(II), Zn(II) and Cu(II) complexes of 5,10,15,20-tetrakis(4′-isopropylphenyl)porphyrin successfully afforded the corresponding 2-bromometalloporphyrins. The β-bromoporphyrin/metalloporphyrins were coupled with three different amines through the creation of the C-N bond by using an economical and air-tolerant photoactive catalyst (NiBr2 · 3H2O) at room temperature under 365 nm radiations. Nickel-catalyzed amination yields are compared with the traditional Buchwald-Hartwig amination yields. Due to the low operational cost, photoinduced nickel-catalyzed C-N couplings were found to be more economical than the Buchwald-Hartwig amination procedure, although the latter afforded higher yields. The nickel-catalyzed photoamination reaction was also extended for the one-pot synthesis of pyridine-3,5-diamine bridged porphyrin dyad. The intramolecular cyclization of the pyridine-3,5-diamine-bridged porphyrin dyad afforded a novel quinolino-fused porphyrin dyad. Degree-and distance-based topological indices of the newly synthesized porphyrins were calculated and correlated with their molar refractivity. All newly synthesized porphyrins are characterized by UV-vis, FTIR, 1H NMR, elemental analysis and mass spectrometry.

Original languageEnglish
Pages (from-to)1054-1065
Number of pages12
JournalJournal of Porphyrins and Phthalocyanines
Issue number8
Publication statusPublished - 1 Aug 2020
Externally publishedYes


  • Buchwald-Hartwig amination
  • meso-tetraarylporphyrins
  • photoamination
  • porphyrin dyad
  • topological indices

ASJC Scopus subject areas

  • General Chemistry


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