Asymmetric phthalocyanine synthesi by ROMP-capture-release

Xiaochun Chen, Thaddeus R. Salmon, Dominic V. McGrath

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Statistical condensation of norbornenyl-tagged phthalonitrile 3 (Pn A) and 4,5-di-4-methoxyphenoxyphthalonitrile 4 (Pn B) followed by ring-opening metathesis polymerization (ROMP) of Pcs AB 3 and B 4 produced asymmetric Pc-appended polymers. Acidic cleavage of the resulting polymers afforded 2,3,9,10,16,17-hexa-(4-methoxyphenoxy)-23-hydroxy Pc 9. A more soluble 2,3,9,10,16,17-hexa-4-pentylphenoxy-23-hydroxy Pc 13 was synthesized by the same strategy and modified with sebacoyl chloride demonstrating that the unmasked hydroxyl site is reactive as a nucleophile.

Original languageEnglish (US)
Pages (from-to)2061-2064
Number of pages4
JournalOrganic Letters
Volume11
Issue number10
DOIs
StatePublished - May 21 2009

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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