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    Exploratory Photochemistry: Pushing the Boundaries of the p-Hydroxyphenacyl Photoremovable Protecting Group

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    Perera_ku_0099D_10615_DATA_1.pdf (2.903Mb)
    Issue Date
    2009-11-30
    Author
    Perera, Chamani
    Publisher
    University of Kansas
    Format
    248 pages
    Type
    Dissertation
    Degree Level
    Ph.D.
    Discipline
    Chemistry
    Rights
    This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
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    Abstract
    Abstract Exploratory Photochemistry: Pushing the Boundaries of the p-Hydroxyphenacyl Photoremovable Protecting Group A. Exploratory and Mechanistic Photochemistry B. Novel Applications of the p-Hydroxyphenacyl Photoremovable Protecting Group By Chamani Perera, Ph.D. Department of Chemistry, November 2009 University of Kansas The p-hydroxyphenacyl (pHP) chromophore is an attractive addition to the family of photoremovable protecting groups in chemistry and biology. Substituent effects on the pHP moiety were explored using cyano substituent at otho and para positions, employing GABA and acetate leaving groups. The quantum yield for GABA release from 3-cyano pHP GABA in water was substantially higher (0.42) than that for the parent. Two novel applications of pHP photochemistry were demonstrated. A light sensitive release of a fluorophore from an almost non-fluorescent pHP fluorophore quencher ensembles resulted in regenerated fluorescence upon exposure to ultraviolet radiation. Carbazole as the quencher leaving group drove the photorelease toward an electron-transfer, radical mechanism. A second application demonstrated that fluorophilic pHP derivatives obtained by attaching a fluorous chain, could be employed to separate the products, often in 95-100% yield, after photorelease from the cage by using fluorous solid phase extraction and fluorous liquid-liquid extraction separation technology.
    URI
    http://hdl.handle.net/1808/6017
    Collections
    • Dissertations [4473]
    • Chemistry Dissertations and Theses [336]

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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