Highly Luminescent Ladderized Fluorene Copolymers Based on B–N Lewis Pair Functionalization

Abdullah F. Alahmadi, Roger A. Lalancette, Frieder Jäkle

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A new B–N functionalized polyaromatic building block for conjugated hybrid polymers is developed. Bromine-functionalized dipyridylfluorene is first subjected to Lewis-base-directed electrophilic borylation and subsequently incorporated into conjugated polymers via transition-metal-catalyzed cross-coupling reactions. The borane monomer exhibits bright blue luminescence in solution, as a result of the rigid ladder-type structure generated upon electrophilic borylation. Yamamoto coupling gives rise to a homopolymer and Stille coupling to a vinylene-bridged copolymer. Polymerization of the BN-fused ladder molecules leads to large bathochromic shifts in absorption and emission, which are most pronounced for the vinylene-bridged copolymer. The polymers display strong luminescence in solution with quantum yields of 55% and 78% and sub-ns fluorescence lifetimes; the copolymer also exhibits bright yellow luminescence in the solid state when precipitated from solution.

Original languageEnglish (US)
Article number1800456
JournalMacromolecular Rapid Communications
Volume39
Issue number22
DOIs
StatePublished - Nov 2018

All Science Journal Classification (ASJC) codes

  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry

Keywords

  • Lewis pairs
  • conjugated polymers
  • isosterism
  • luminescent polymers
  • organoboranes

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