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CONJUGATED ORGANOPHOSPHORUS MATERIALS AND THEIR TRANSITION METAL COMPLEXES

Grimm, Alexandra Beckman
http://rave.ohiolink.edu/etdc/view?acc_num=case1477930036104679

Abstract Details

2016, Doctor of Philosophy, Case Western Reserve University, Chemistry.
2-R-1,3-Benzoxaphospholes (R-BOPs) are a class of highly fluorescent molecules that possess a P=C bond and display possible application in OLEDs, solar photovoltaics, and other electroluminescent devices. In order to expand these fluorescent molecules to fluorescent polymers incorporating low-coordinate phosphorus, we sought to synthesize conjugated polymers via palladium-catalyzed cross coupling. Efforts towards synthesizing these conjugated polymers are reported. Initial efforts towards synthesizing conjugated polymers were unsuccessful. Results indicate halide substituted R-BOPs as unsuitable in palladium-catalyzed coupling due to possible oxidation. An important step of Suzuki-Miyaura coupling is oxidative addition. To better understand the reaction of BOPs that proceeds under Suzuki-Miyaura coupling, the oxidative addition of these molecules was examined. Results indicated that 2-(p-bromophenyl)-1,3-benzoxaphoshpole interacts with metals, but does not produce one product that is easily isolated. Results of 2-(o-bromophenyl)-1,3-benzoxaphosphole indicated that no interactions with metals occur. During examination of 2-phenyl-1,3-benzoxaphosphole, two novel dimetallic complexes were isolated and analyzed by single crystal X-ray diffraction. Since it was shown that metals could bind to BOPs, and in order to protect and kinetically stabilize the P=C bond within the BOP, novel (¿1-2-R-1,3-benzoxaphosphole-P)pentacarbonyl tungsten (0) complexes were synthesized and characterized by multi-nuclear magnetic resonance spectroscopy (NMR), elemental analysis (EA), and single-crystal X-ray diffraction (X-ray). The synthesis, characterization, and comparison to their R-BOP counterparts are reported. These complexes were then employed in Suzuki-Miyaura cross coupling reactions. The synthesis and ongoing investigation into the unknown product of these reactions is discussed.
John Protasiewicz, D (Advisor)
Genevieve Sauve (Committee Chair)
293 p.
Chemistry; Inorganic Chemistry
organometallic, dimetallic, low coordinate phosphorus

Recommended Citations

Citations

  • Grimm, A. B. (2016). CONJUGATED ORGANOPHOSPHORUS MATERIALS AND THEIR TRANSITION METAL COMPLEXES [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1477930036104679

    APA Style (7th edition)

  • Grimm, Alexandra. CONJUGATED ORGANOPHOSPHORUS MATERIALS AND THEIR TRANSITION METAL COMPLEXES. 2016. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1477930036104679.

    MLA Style (8th edition)

  • Grimm, Alexandra. "CONJUGATED ORGANOPHOSPHORUS MATERIALS AND THEIR TRANSITION METAL COMPLEXES." Doctoral dissertation, Case Western Reserve University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=case1477930036104679

    Chicago Manual of Style (17th edition)

case1477930036104679
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© 2016, some rights reserved.Creative Commons License CONJUGATED ORGANOPHOSPHORUS MATERIALS AND THEIR TRANSITION METAL COMPLEXES by Alexandra Beckman Grimm is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. Based on a work at etd.ohiolink.edu.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.