Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs)

Nuha Alharbi, Alejandro Diaz-Moscoso, Graham J. Tizzard, Simon J. Coles, Michael J. Cook, Andrew N. Cammidge

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

New tetrabenzotriazaporphyrins are reported that are functionalised at the meso-position. The derivatives functionalised with meso-bromophenyl substituents are synthesised using an improved variation on the traditional reaction between phthalonitriles and Grignard reagents. For all other new derivatives, a modern protocol is employed that gives convenient access to these challenging materials by template co-macrocyclisation between phthalonitriles and aryl-aminoisoindoline derivatives like 15. The newly developed procedure allows design and synthesis of elaborate, functional composites and this is demonstrated by synthesis of meso-pyrenylTBTAP 24, a linked double chromophore in which the two complementary units lie perpendicular to each other and therefore have minimal ground state interaction.
Original languageEnglish
Pages (from-to)7370-7379
Number of pages10
JournalTetrahedron
Volume70
Issue number40
Early online date26 Jun 2014
DOIs
Publication statusPublished - 7 Oct 2014

Keywords

  • Phthalocyanines
  • Porphyrins
  • Heterocycles
  • Synthesis
  • Hybrids
  • Pyrene

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