Convenient syntheses of phthalocyanine and tetrabenzotriazaporphyrin (TBTAP) mono-alkynes; unhindered building blocks for click chemistry and beyond

Ateyat Allah Aljuhani, Alejandro Diaz-Moscoso, Andrew N. Cammidge

Research output: Contribution to journalArticlepeer-review

Abstract

Unsymmetrical phthalocyanines and related macrocycles are often desirable for covalent construction or the self-assembly of more complex architectures. Terminal alkynes are versatile in this regard because they are amenable to cross-coupling via Sonogashira-type reactions, alkyne-alkyne coupling via Glaser-type couplings, and triazole formation via Click reaction with azides. Here we describe two complementary syntheses to conveniently add a single alkyne onto the phthalocyanine peripheral position and onto the meso-phenyl group of an (aryl)tetrabenzotriazaporphyrin, here providing a remote link point that is insulated from the macrocycle.
Original languageEnglish
Pages (from-to)408-413
Number of pages6
JournalJournal of Porphyrins and Phthalocyanines
Volume27
Issue number01n04
Early online date2 Mar 2023
DOIs
Publication statusPublished - Apr 2023

Keywords

  • Alkynes
  • Click Chemistry
  • Cross-Coupling
  • Phthalocyanine-Porphyrin hybrids
  • Unsymmetrical Phthalocyanines

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