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Boron containing vinyl aromatic polymers
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Text
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Title
Boron containing vinyl aromatic polymers
SubTitle
synthesis, characterization and applications
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ETD_1533
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http://hdl.rutgers.edu/1782.2/rucore10002600001.ETD.000051311
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eng
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theses
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Topic
Chemistry
Subject
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(authority = ETD-LCSH)
Topic
Boron compounds
Subject
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(authority = ETD-LCSH)
Topic
Boron compounds--Synthesis
Subject
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(authority = ETD-LCSH)
Topic
Polymeric composites
Abstract
Novel luminescent polystyrene-based organoborane polymers were synthesized via facile silicon-boron exchange reactions with boron tribromide. The Lewis acidity as well as the photophysical properties of the polymers were then fine tuned by variation of the organic pi-system. The key step is a selective boron-tin exchange that allows for controlled and selective replacement of one of the bromine substituents by the chromophoric system, followed by substitution of the second bromine by a sterically hindered aryl group. The polymers and model compounds were fully characterized by multinuclear NMR spectroscopy. Molecular weights were determined by GPC. DSC and TGA were used to determine their thermal properties. Both polymers and model systems are highly emissive and UV-visible and fluorescence spectroscopy were used to ascertain their photophysical characteristics. To probe the use of the polymers as potential anion sensors, they were subjected to complexation with fluoride ([Bu4N]F in THF) and their complexation was studied by 11B NMR as well as UV-vis and fluorescence spectroscopy.
To counter the oxidative degradation of the systems a new strategy was adapted in which we prepared stannylcarbazole precursors which would act as chromophores. To further enhance the stability of the boron center in these systems the mesityl group was replaced by the bulkier 1,3,5-triisopropylphenyl group. The models and polymers synthesized show superior stability as compared to the compounds synthesized earlier. The compounds are also highly emissive in the blue region.
Systems that contain electroactive ferrocenyl groups in the side-chain of polystyrene were also synthesized. Cyclic voltammetry studies confirm the electroactive nature of these polymers. A quasi-reversible boron redox couple and a ferrocene-centered redox process were observed.
Finally, a trimethylsilyl-functionalized vinyl bithiophene monomer was prepared. This monomer was polymerized by a variety of methods including standard free radical polymerization (BPO, AIBN), via nitroxide-mediated polymerization (NMP) and also by anionic polymerization. Moderate molecular weights in the range of 4000 – 9000 were obtained.
To counter the oxidative degradation of the systems a new strategy was adapted in which we prepared stannylcarbazole precursors which would act as chromophores. To further enhance the stability of the boron center in these systems the mesityl group was replaced by the bulkier 1,3,5-triisopropylphenyl group. The models and polymers synthesized show superior stability as compared to the compounds synthesized earlier. The compounds are also highly emissive in the blue region.
Systems that contain electroactive ferrocenyl groups in the side-chain of polystyrene were also synthesized. Cyclic voltammetry studies confirm the electroactive nature of these polymers. A quasi-reversible boron redox couple and a ferrocene-centered redox process were observed.
Finally, a trimethylsilyl-functionalized vinyl bithiophene monomer was prepared. This monomer was polymerized by a variety of methods including standard free radical polymerization (BPO, AIBN), via nitroxide-mediated polymerization (NMP) and also by anionic polymerization. Moderate molecular weights in the range of 4000 – 9000 were obtained.
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electronic resource
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xxi, 163 p. : ill.
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Ph.D.
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Includes bibliographical references (p. 146-161)
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by Kshitij K. Parab
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Kshitij K.
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Kshitij K. Parab
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Jordan
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Frank
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Frank Jordan
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Jäkle
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Frieder
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Frieder Jäkle
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Sheridan
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John
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John B Sheridan
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He
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Huixin
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Huixin He
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Peetz
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Ralf
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Ralf Peetz
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Rutgers University
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Graduate School - Newark
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2009
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2009-05
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xx
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Rutgers University Electronic Theses and Dissertations
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ETD
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Graduate School - Newark Electronic Theses and Dissertations
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rucore10002600001
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doi:10.7282/T3N58MKT
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ETD doctoral
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The author owns the copyright to this work.
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Copyright protected
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Open
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Parab
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Kshitij
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Kshitij Parab
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Rutgers University. Graduate School - Newark
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I hereby grant to the Rutgers University Libraries and to my school the non-exclusive right to archive, reproduce and distribute my thesis or dissertation, in whole or in part, and/or my abstract, in whole or in part, in and from an electronic format, subject to the release date subsequently stipulated in this submittal form and approved by my school. I represent and stipulate that the thesis or dissertation and its abstract are my original work, that they do not infringe or violate any rights of others, and that I make these grants as the sole owner of the rights to my thesis or dissertation and its abstract. I represent that I have obtained written permissions, when necessary, from the owner(s) of each third party copyrighted matter to be included in my thesis or dissertation and will supply copies of such upon request by my school. I acknowledge that RU ETD and my school will not distribute my thesis or dissertation or its abstract if, in their reasonable judgment, they believe all such rights have not been secured. I acknowledge that I retain ownership rights to the copyright of my work. I also retain the right to use all or part of this thesis or dissertation in future works, such as articles or books.
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