• Login
    View Item 
    •   Oxy Scholar Home
    • Chemistry
    • Chemistry URC Student Scholarship
    • View Item
    •   Oxy Scholar Home
    • Chemistry
    • Chemistry URC Student Scholarship
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Toward the Synthesis of a Topologically Non-Planar Porphyrin

    Thumbnail
    Author
    Ro, Edward
    Issue
    urc_student; urc_student
    Date
    2010-01-01 0:00
    Metadata
    Show full item record
    URI
    https://scholar.oxy.edu/handle/20.500.12711/549
    Abstract
    Topology is an area of mathematics concerned with spatial properties that are preserved under deformation. When applied to chemistry it allows stretching of bonds and bending of structure, but no breaking. A topologically planar molecule is one that has been deformed to become planar; however, there cannot be any crossing over between bonds. A porphyrin molecule is a macrocyclic organic molecule that consists of four pyrroles attached to each other by methine bridges. In order to have a topologically non-planar porphyrin, two straps must be introduced in order to bridge the molecule. Addition of a metal to the center of the molecule results in a topologically non-planar porphyrin. The synthetic route to the base porphyrin started with α-bromo-ο-tolunitrile and sodium methoxide to produce α-methoxy-ο tolunitrile. The tolunitrile was reduced with dibal and hydrolyzed with hydrochloric acid/water to form α-methoxy-ο-tolualdehyde. Subsequently, the tolualdehyde was combined with pyrrole to form a ?half porphyrin,? called a dipyrromethane. The final step in the synthesis of the base porphyrin combined the dipyrromethane and α-bromo-ο-tolualdehyde, with boron trifluoride catalyst. Different atropisomers were characterized by ?H NMR as the methoxy groups exhibited varying chemical shifts and peaks. Heating the porphyrin to 70?C appeared to rotate the methoxy groups, overcoming the problem of having multiple atropisomers. Various attempts at introducing straps to the base porphyrin have been inconclusive.
    Collections
    • Chemistry URC Student Scholarship

    Browse

    All of Oxy ScholarCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsJournal TitleJournal IssueThis CollectionBy Issue DateAuthorsTitlesSubjectsJournal TitleJournal Issue

    My Account

    LoginRegister

    DSpace software copyright © 2002-2021  DuraSpace
    Contact Us | Send Feedback
    DSpace Express is a service operated by 
    Atmire NV