Substituent-controlled construction of A4B2-hexaphyrins and A3B-porphyrins: a mechanistic evaluation

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ÇINAR S., Tasgin D. I., ÜNALEROĞLU C.

Beilstein Journal of Organic Chemistry, vol.19, pp.1832-1840, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 19
  • Publication Date: 2023
  • Doi Number: 10.3762/bjoc.19.135
  • Journal Name: Beilstein Journal of Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, Chemical Abstracts Core, Directory of Open Access Journals
  • Page Numbers: pp.1832-1840
  • Keywords: A3B-porphyrin, A4B2-hexaphyrin, Cu(OTf)2 catalysis, HRESI–TOF analysis, N-tosylimine
  • Hacettepe University Affiliated: Yes

Abstract

A substituent-dependent construction of novel A3B-porphyrins along with A4B2-hexaphyrins was realized by the reactions of N-tosylimines and meso-aryl-substituted tripyrranes in the presence of Cu(OTf)2 as the catalyst. The reaction mechanism of the presented method was studied on model reactions by electrospray-ionization time-of-flight (HRESI–TOF) mass spectral analysis in a timely manner. The analytical results indicated that the observed azafulvene-ended di- and tripyrrolic intermediates are responsible for the formation of porphyrinogen and hexaphyrinogen forms.