Title page for ETD etd-11162005-180657

Type of Document Dissertation
Author Ongayi, Caroline Owendi
Author's Email Address congay1@lsu.edu
URN etd-11162005-180657
Title Synthesis of Symmetric and Asymmetric Water-Soluble Porphyrin Derivatives
Degree Doctor of Philosophy (Ph.D.)
Department Chemistry
Advisory Committee
Advisor Name Title
Maria da Graca H. Vicente Committee Chair
Robert Hammer Committee Member
William Crowe Committee Member
William Daly Committee Member
Ronald Malone Dean's Representative
  • synthesis
  • biliverdins
  • corroles
  • water-soluble
  • porphyrins
Date of Defense 2005-11-11
Availability unrestricted
Novel symmetric and asymmetric water-soluble tetrabenzoporphyrin are synthesized in relatively good yields. These compounds are synthesized by the condensation of butanopyrrole with several aldehydes that contain masked water solubilizing groups followed by metal insertion, oxidation and demetallation and deprotection of the masked solubilizing groups. The biological evaluation (in vitro and in vivo) studies are described in addition to the photophysical evaluations of the corresponding compounds.

A novel versatile route to the syntheses of novel free-bases and metallo-benzoylbiliverdin is discussed. The treatment of metal free-dodecasubstituted porphyrin with sodium nitrite and trifluoroacetic acid at room temperature in the presence of oxygen affords ring-opened benzoylbiliverdin in 77-80% yields. These compounds are metallated with several diamagnetic metal ions and their structures confirmed by NMR and X-Ray crystallography. Tetramerization of excess butanopyrrole and several aldehydes also afforded novel metallo-butanocorroles and metallo-benzocorrole. The structures of these compounds are also analysed using MS (MALDI), NMR and X-Ray crystallography.

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