Photoinduced copper(I)-catalyzed click chemistry by the electron transfer process using polynuclear aromatic compounds

Gorkem Yilmaz, Birol Iskin, Yusuf Yagci*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)

Abstract

Based on electron-transfer reactions of the excited states of polynuclear aromatic compounds, such as anthracene, pyrene, and phenothiazine and Cu(II), a long-wavelength photoinduced copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction is developed. Although at different rates, all the sensitizers are shown to efficiently reduce Cu(II) to Cu(I), which catalyzes the click reaction between small organic compounds. The applicability of the method for the construction of various macromolecular architectures, including telechelic polymers and block copolymers is demonstrated. Spectroscopic and chromatographic investigations reveal that successful macromolecular syntheses are achieved. A photoinduced copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction using polynuclear aromatic compounds and Cu(II) is developed. Although at different rates, all the sensitizers efficiently reduce Cu(II) to Cu(I), which catalyzes the click reaction between model organic compounds. The applicability of the method for the construction of various macromolecular architectures including telechelic polymers and block copolymers is demonstrated.

Original languageEnglish
Pages (from-to)662-668
Number of pages7
JournalMacromolecular Chemistry and Physics
Volume215
Issue number7
DOIs
Publication statusPublished - Apr 2014

Keywords

  • click chemistry
  • photochemical processes
  • polymer modification
  • redox processes

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