Synthesis and characterization of polymeric thioxanthone photoinitatiors via double click reactions

Gacal B., Akat H., Balta D., ARSU N., Yağcı Y.

MACROMOLECULES, vol.41, no.7, pp.2401-2405, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 41 Issue: 7
  • Publication Date: 2008
  • Doi Number: 10.1021/ma702502h
  • Journal Name: MACROMOLECULES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2401-2405
  • Yıldız Technical University Affiliated: Yes

Abstract

Macrophotoinitiators containing thioxanthone (TX) moieties as side chains were synthesized by using "double click chemistry" strategy; combining in-situ 1,3-dipolar azide-alkyne [3 + 2] and thermoreversible Diels-Alder (DA) [4 + 2] cycloaddition reactions. For this purpose, thioxanthone-anthracene (TX-A), N-proparayl-7-oxynorbornene (PON), and polystyrene (PS) with side-chain azide moieties (PS-N-3) were reacted in N,N-dimethylformamide (DMF) for 36 h at 120 degrees C. In this process, PON acted as a "click linker" since it contains both protected maleimide and alkyne functional groups Suitable for 1,3-dipolar azide-alkyne and Diels-Alder click reactions, respectively. This way, the aromacity of the central phenyl unit of the anthracene moiety present in TX-A was transformed into TX chromophoric groups. The resulting polymers possess absorption characteristics similar to the parent TX. Their capabilities to act as photoinitiator for the polymerization of mono-and multifunctional monomers, namely methyl methacrylate (MMA) and 1,1,1-tris(hydroxymethyl)propane triacrylate (TPTA) were also examined.