Various polycarbonate graft copolymers via Diels-Alder click reaction

Dag A., Aydin M., Durmaz H., Hızal G., Tunca Ü.

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, vol.50, no.21, pp.4476-4483, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 50 Issue: 21
  • Publication Date: 2012
  • Doi Number: 10.1002/pola.26254
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4476-4483
  • Keywords: aliphatic polycarbonate, biocompatibility, biodegradable, click reaction, Diels-Alder reaction, furan-protected maleimide terminated-poly(ethylene glycol), furan-protected maleimide terminated-poly(methyl methacrylate), graft copolymers, NMR spectroscopy, ring opening polymerization, triple detection GPC, UV-vis spectroscopy, RING-OPENING POLYMERIZATION, STAR BLOCK-COPOLYMERS, CYCLIC CARBONATE, FUNCTIONALIZATION, CONSTRUCTION, TERPOLYMERS, CONJUGATION, POLYMERS, MONOMER
  • Bezmialem Vakıf University Affiliated: Yes


In this work, we used DielsAlder click reaction for the preparation of various types of aliphatic polycarbonates (PCs). We first prepared a novel anthracene-functionalized cyclic carbonate monomer, anthracen-9-ylmethyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (2), followed by ring-opening polymerization of this monomer to prepare PC with pendant anthracene groups (PC-anthracene) using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)/1-(3,5-bis(trifloromethyl)phenyl)-3-cyclohexylthiourea (TU) as the catalyst and benzyl alcohol as the initiator in CH2Cl2 at room temperature. Subsequently, the resulting PC-anthracene (Mn,TDGPC = 6000 g/mol, Mw/Mn = 1.22) was grafted with a linear alpha-furan protected-maleimide terminated-poly(methyl methacrylate) (PMMA-MI) (Mn,GPC = 3100 g/mol, Mw/Mn = 1.31), or poly(ethylene glycol) (PEG-MI) (Mn,GPC = 550 g/mol, Mw/Mn = 1.09), or a mixture of PMMA-MI and PEG-MI to yield well-defined PC graft or hetero graft copolymers, PC-g-PMMA (Mn,TDGPC = 59000 g/mol, Mw/Mn = 1.22) or PC-g-PEG, or PC-g-(PMMA)-co-PC-g-(PEG) (Mn,TDGPC = 39900 g/mol, Mw/Mn = 1.16), respectively, using DielsAlder click reaction in toluene at 110 degrees C. The DielsAlder grafting efficiencies were found to be over 97% using UV spectroscopy. Moreover, the structural analyses and the molecular weights of resulting graft copolymers were determined via 1H NMR and triple detection GPC (TD-GPC), respectively. (c) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012