(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.
ASJC Scopus subject areas
- Organic Chemistry