Asymmetric phthalocyanine synthesi by ROMP-capture-release

Xiaochun Chen, Thaddeus R. Salmon, Dominic V Mcgrath

Research output: Contribution to journalArticle

8 Citations (Scopus)

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

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metathesis
Ring opening polymerization
Polymerization
Polymers
polymerization
Nucleophiles
nucleophiles
rings
polymers
Hydroxyl Radical
cleavage
Condensation
Catalytic Domain
condensation
chlorides
phthalocyanine
sebacoyl chloride

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Asymmetric phthalocyanine synthesi by ROMP-capture-release. / Chen, Xiaochun; Salmon, Thaddeus R.; Mcgrath, Dominic V.

In: Organic Letters, Vol. 11, No. 10, 21.05.2009, p. 2061-2064.

Research output: Contribution to journalArticle

Chen, Xiaochun ; Salmon, Thaddeus R. ; Mcgrath, Dominic V. / Asymmetric phthalocyanine synthesi by ROMP-capture-release. In: Organic Letters. 2009 ; Vol. 11, No. 10. pp. 2061-2064.
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