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Engineering of Novel Task-specific Ionic Liquids for the Selective Extraction and Preconcentration of DNA and Emerging Contaminants

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2013, Doctor of Philosophy, University of Toledo, Chemistry.
Ionic liquids (ILs) are a class of non-molecular solvents comprised of organic cations and organic or inorganic anions. The unique properties of ILs include their wide viscosity ranges, nearly no measurable vapor pressure, high thermal stability, and a multitude of varying solvation interactions. These properties make them an attractive class of solvents in varying extraction techniques. The first part of this dissertation describes an introduction of ionic liquids and their applications in extraction techniques. Chapters 2-4 introduce application of ILs as solvents in the extraction and preconcentration of various analytes using microextraction techniques. Task-specific ILs were applied for the first time as solvents in the extraction and preconcentration of deoxyribonucleic acid (DNA) from sample matrix using an in situ dispersive liquid-liquid microextraction (DLLME) approach. The effect of different IL substituents and functional groups on the extraction efficiency of DNA was investigated. Interactions between the ILs and DNA were studied using 31P NMR. Subsequently, magnetic ionic liquids (MILs) were introduced in the extraction of DNA from aqueous samples. The extraction process can be completed in 1 minute without employing a centrifugation step, and high extraction efficiency of DNA was obtained. Back isolation of DNA from the MIL was also investigated. Additionally, the IL-based DLLME was applied for the extraction of 14 emerging contaminants from aqueous sample. The selectivities and sensitivities of this method can be controlled by utilizing ILs containing various functional groups as substituents to the cationic moiety of the IL. Boronic acids and their corresponding pinacolboronate esters play an important role in the Suzuki-Miyaura coupling reaction. The second part of this dissertation describes the application of ionic liquids as the complexing reagent to improve the separation of boronic acid from the corresponding boronate ester. Chapter 6 presents a study utilizing two new glucaminium-based ILs to form complex with 2-aminopyrimide-5-ylboronic acid (2-APYBA), which is often an impurity in 2-aminopyrimidine-5-pinacolboronate ester (2-APPBE). The complexation between the glucaminium-based ILs and 2-APYBA was confirmed by 11B NMR. The method was successfully employed for the quantification of 2-APYBA in a real 2-APPBE sample.
Jared Anderson (Committee Chair)
Dragan Isailovic (Committee Member)
Jon Kirchhoff (Committee Member)
Amanda Bryant-Friedrich (Committee Member)
181 p.

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Citations

  • Li, T. (2013). Engineering of Novel Task-specific Ionic Liquids for the Selective Extraction and Preconcentration of DNA and Emerging Contaminants [Doctoral dissertation, University of Toledo]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1384515987

    APA Style (7th edition)

  • Li, Tianhao. Engineering of Novel Task-specific Ionic Liquids for the Selective Extraction and Preconcentration of DNA and Emerging Contaminants. 2013. University of Toledo, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=toledo1384515987.

    MLA Style (8th edition)

  • Li, Tianhao. "Engineering of Novel Task-specific Ionic Liquids for the Selective Extraction and Preconcentration of DNA and Emerging Contaminants." Doctoral dissertation, University of Toledo, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1384515987

    Chicago Manual of Style (17th edition)