Modification of alkyne-functionalized asymmetric phthalocyanines by CuI-catalyzed azide-alkyne cycloaddition

Xiaochun Chen, Chin Wei Lu, Yiming Huang, Dominic V. McGrath

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The use of asymmetric phthalocyanines (Pcs) as platforms for the preparation of several asymmetric hexatriazolyl-monohydroxyphthalocyanines via copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction was investigated. Asymmetric Pcs 5a and 5b were prepared through statistical macrocyclization of phthalonitriles (Pns) 1a and 2 to give PMB-protected 4a and 4b, which afforded asymmetric Pcs 5a and 5b after acidic cleavage. The 'ROMP-Capture-Release' method as a synthetic approach to prepare asymmetric Pc 5b was also evaluated. TIPS-protection of the terminal alkynes was necessary to prevent cross-coupling during the ring-opening metathesis polymerization (ROMP) step. Zinc Pc 5b was successfully used as a scaffold for functional modification under CuAAC conditions using several azides bearing hydrophobic, photo-crosslinkable, or electroactive moieties. Monitoring the CuAAC reaction by both UV/Vis and FTIR spectroscopies provided insight into the role of azide equivalent, reaction time, and catalyst on reaction progress.

Original languageEnglish (US)
Pages (from-to)9154-9160
Number of pages7
JournalTetrahedron
Volume71
Issue number48
DOIs
StatePublished - Dec 2 2015

Keywords

  • Click chemistry
  • Cycloaddition
  • Metathesis
  • Phthalocyanine
  • Tetrapyrrolic molecules

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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