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, cilt.19, ss.1832-1840, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 19
  • Basım Tarihi: 2023
  • Doi Numarası: 10.3762/bjoc.19.135
  • Dergi Adı: Beilstein Journal of Organic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, Chemical Abstracts Core, Directory of Open Access Journals
  • Sayfa Sayıları: ss.1832-1840
  • Anahtar Kelimeler: A3B-porphyrin, A4B2-hexaphyrin, Cu(OTf)2 catalysis, HRESI–TOF analysis, N-tosylimine
  • Hacettepe Üniversitesi Adresli: Evet

Özet

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.