Synthesis and Structure-Property Relationships in Regioisomeric Alternating Borane-Terthiophene Polymers

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

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Main-chain boron-containing π-conjugated polymers are attractive for organic electronic, sensing, and imaging applications. Alternating terthiophene-borane polymers were prepared and the effects of regioisomeric attachment of the conjugated linker and variations in the electronic effect of the pendent aryl groups (2,4,6-tri-tert-butylphenyl, Mes*; 2,4,6-tris(trifluoromethyl)phenyl, FMes) examined. Pd2dba3/P(t-Bu)3-catalyzed Stille polymerization of arylbis(2-thienyl)borane and arylbis(3-thienylborane) with 2,5-bis(trimethylstannyl)thiophene at 120 °C gave polymers with appreciable molecular weight but MALDI-TOF MS analyses showed evidence of unusually prominent homocoupling. These defects could be suppressed by using brominated rather than iodinated monomers, more hindered 2,5-bis(tri-n-butylstannyl)thiophene as comonomer, and Pd2dba3/P(o-tol)3 as the catalyst at 100 °C. Under these conditions, macrocyclic species with n=3–10 repeating units formed preferentially according to MALDI-TOF MS analyses. Photophysical studies revealed a prominent effect of the regiochemistry and the nature of the pendent aryl groups on the absorption and emission, giving rise to orange, yellow-green, blue-green, and blue emissive materials respectively. The electronic effects were rationalized through DFT calculations on bis(terthiophene) model systems.

Original languageEnglish (US)
Article numbere202203619
JournalChemistry - A European Journal
Issue number18
StatePublished - Mar 28 2023

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


  • boron
  • conjugated materials
  • organoborane
  • polymers
  • thiophene


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