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Lewis Base Adducts of Borafluorene: En Route to Polymers and the Discovery of New Luminescent Adducts

  • Author / Creator
    Berger, Christopher J.
  • A series of novel Lewis base monoadducts of 9-bromo-9-borafluorene (BrBFl•LB, LB = IPr, IPrCH2, PPh3) and the bisadduct [(DMAP)2BFl]Br were prepared and underwent reactivity studies in the pursuit of incorporating a borafluorene unit into a polymeric scaffold for the sensing of nucleophiles in solution. This was to be accomplished through the functionalization of these adducts at boron, polymerization and subsequent removal of the Lewis base. Although initial studies indicated that the removal of the Lewis base was more difficult than anticipated, the adducts BrBFl•PPh3, [(DMAP)2BFl]Br and BrBFl•IPrCH2 were found to be fluorescent. This observation was initially counterintuitive, as a borafluorene containing a four-coordinate boron environment would not be expected to possess such a property. Theoretical studies were conducted to determine the nature of the fluorescence and revealed that the Lewis base bonded to boron significantly contribute to the transitions leading to fluorescence.

  • Subjects / Keywords
  • Graduation date
    2013-11
  • Type of Item
    Thesis
  • Degree
    Master of Science
  • DOI
    https://doi.org/10.7939/R3610W33M
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
  • Language
    English
  • Institution
    University of Alberta
  • Degree level
    Master's
  • Department
    • Department of Chemistry
  • Supervisor / co-supervisor and their department(s)
    • Rivard, Eric (Chemistry)
  • Examining committee members and their departments
    • Veinot, Jonathan (Chemistry)
    • West, Frederick (Chemistry)