A unique stepped multifunctionality of perfluorinated aryl compound and its versatile use in synthesizing grafted polymers with controlled structures and topologies

Zhenhua Zhao, Xiaohua Ma, Aixin Zhang, Naiheng Song*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A unique stepped multifunctionality of perfluorinated aryl compound for the first time was studied by using model reactions between 2,5- dipentafluorophenyl-1,3,4-oxadiazole (FPOx) and mono functional p-cresol at different reaction conditions. Four distinctively different levels of reactivity were discovered for the para and ortho C-F of FPOx, which could be easily triggered by the reaction temperature in the range of r.t. to 160 °C. C-F of all levels of reactivity could react quantitatively with nucleophiles (such as phenoxide); and by controlling the reaction conditions, the low-level-reactivity C-F would not interfere with the reaction of C-F of higher reactivity. Application of this multistepped reactivity of FPOx in quantitative postpolymerization functionalization of polymer was successfully demonstrated. Stoichiometric amount of p-cresol, with the molar feed ratio of p-cresol in relative to the repeat unit of the polymer of FPOx and 6F-BPA in the range of 1-4, could be readily grafted onto the polymer by simply controlling the reaction temperature. FPOx-based, versatile one-pot synthesis of high molecular-weight grafted polymers with well-controlled structures and topologies were also demonstrated.

Original languageEnglish (US)
Pages (from-to)2423-2433
Number of pages11
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume49
Issue number11
DOIs
StatePublished - Jun 1 2011

Keywords

  • controlled polymer synthesis
  • functionalization of polymers
  • perfluorinated aromatics
  • polyethers
  • quantitative functionalization
  • stepped multifunctionality
  • synthesis
  • topology

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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