ROM polymerization-capture-release strategy for the chromatography-free synthesis of novel unsymmetrical porphyrazines

Matthew J. Fuchter, Benjamin J. Vesper, Karen A. Murphy, Hazel A. Collins, David Phillips, Anthony G.M. Barrett*, Brian M Hoffman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

(Chemical Equation Presented) Crossover-Linstead macrocyclization reactions of two norbornenyl-tagged diaminomaleonitriles with dipropylmaleonitrile gave access to crude mixtures of porphyrazines containing diamino-hexapropyl- porphyrazine magnesium complexes. The mixtures were subjected to ring-opening metathesis polymerization to yield the insoluble diaminoporphyrazine- functionalized polymers. Acid-mediated cleavage from the polymer backbone followed by acylation of the resultant sensitive macrocyclic diamines gave monoacetyl-, monotrifluoroacetyl-, and ditrifluoroacetyl-substituted porphyrazinediamines. Conversion of these amido-porphyrazines to the corresponding zinc macrocycles and studies of their electronic absorption and emission spectra, electrochemistry, and photophysics are described.

Original languageEnglish (US)
Pages (from-to)2793-2802
Number of pages10
JournalJournal of Organic Chemistry
Volume70
Issue number7
DOIs
StatePublished - Apr 1 2005

ASJC Scopus subject areas

  • Organic Chemistry

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