ROM polymerization-capture-release: Application to the synthesis of unsymmetrical porphyrazinedithiols and peripherally metalated derivatives

Matthew J. Fuchter, Brian M. Hoffman*, Anthony G.M. Barrett

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

Crossover Linstead macrocyclization of a doubly norbornenyl-functionalized dimercaptomaleonitrile with dipropylmaleonitrile gave a crude mixture of porphyrazines containing the hexapropylporphyrazinedithiol magnesium complex. The mixture was subjected to ring-opening metathesis polymerization to yield the insoluble porphyrazinedithiol-functionalized polymers. Cleavage from the polymer backbone using mercury(II) acetate followed by reaction with electrophiles gave access to a range of thioporphyrazinedithiol derivatives including solitaire porphyrazines. Studies into the possible uses of hexapropyl-2,3-di-(carboxymethylthio)porphyrazine in sensing metal cations in solution are described.

Original languageEnglish (US)
Pages (from-to)5086-5091
Number of pages6
JournalJournal of Organic Chemistry
Volume70
Issue number13
DOIs
StatePublished - Jun 24 2005

ASJC Scopus subject areas

  • Organic Chemistry

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