Polystyrene end-labeled with 2,7-dibromofluorene synthesized using an adaptation of reverse atom transfer radical polymerization

Bellamarie Ludwig, Eric S. Tillman

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Polystyrene with high amounts of end-labeling was synthesized using iniuating systems comprised of conventional radical initiators and 2,7-dibromofluorene or other fluorene derivatives in an adaptatioo of reverse atom transfer radical polymerization (RATRP). Benzoyl peroxide (BPO) or 2,2′-azoisobutyronitrile (AIBN) were decomposed and allowed to react with 2,7-dibromofluorene, 2-bromofluorene, or fluorene in the presence of ligand-bound CuX2 allowing for abstraction of the 9-H from the flouorenyl species and the establishment of an equilibrium between the subsequent active radical and the dormant alkyl halide. Gel permeation chromatography (GPC) traces indicated CuCl2-catalyzed reactions produced polymers possessing narrow polydispersity index (PDI) values <1.3 with AIBN and 2,7-dibromofluorene systems, while analogous reactions catalyzed using CuBr2 were less controlled (PDI > 1.7). Analysis of the polymers using UV-vis spectroscopy and UV-GPC demonstrated competition between initiation from both the conventional radical initiator and fluorenyl species generating polymers end-labeled with both the 2,7-dibromofluorene and isobutyronitrile groups. Fluorene or 2-bromofluorene as co-initiators led to lowered amounts of end-labeling, but the polymers generally possessed lower PDI values compared to 2,7-dibromofluorene systems.

Original languageEnglish (US)
Pages (from-to)2143-2152
Number of pages10
JournalMacromolecular Chemistry and Physics
Issue number21
StatePublished - Nov 1 2005

All Science Journal Classification (ASJC) codes

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry


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