Title page for ETD etd-10232007-121548

Type of Document Dissertation
Author Jiao, Lijuan
Author's Email Address ljiao1@lsu.edu
URN etd-10232007-121548
Title Synthesis and Functionalizations of Tetrapyrrole Derivatives
Degree Doctor of Philosophy (Ph.D.)
Department Chemistry
Advisory Committee
Advisor Name Title
Kevin M. Smith Committee Chair
Brian Hales Committee Member
M. Graca H. Vicente Committee Member
William Crowe Committee Member
James E. Henry Dean's Representative
  • tetrapyrrole
  • synthesis
  • porphycene
  • benzoporphyrin
  • methylenepropanoporphyrin
Date of Defense 2007-07-02
Availability unrestricted
Chapter 1 of this Dissertation presents a brief overview of the history of tetrapyrrole derivatives and of their fundamental properties. Overviews of porphyrins, benzoporphyrins, chlorins and porphycenes are presented.

Work presented in Chapter 2 through Chapter 4 mainly focuses on the syntheses and functionalization of chromophore-extended porphyrin derivatives. Several new synthetic routes for the syntheses and functionalizations of extended porphyrins either at the β-position or at the meso-position of porphyrin are developed. From these improved synthetic routes, the regio-selective syntheses of porphyrin derivatives are described. Chapter 2 mainly focuses on the syntheses of β,β'-fused methylenepropanoporphyrins and related porphyrin dimers. Chapter 3 mainly describes a new synthetic route for selective synthesis of benzoporphyrin regioisomers and Chapter 4 mainly discusses new work on the efficient synthesis of the so-called "Hangman Porphyrin" analogs.

Chapter 5 consists two parts. The first part is devoted results of work on the total synthesis of an important porphycene derivative, 9-capronyl-oxytetrakis(methyoxyethyl)-porphycene, which has already been shown to have attractive potential applications in photodynamic therapy of tumors. The second part of Chapter 5 concerns the improved syntheses of 2,2'-bipyrrole, which is an important part of our effort to improve the synthesis of porphycene and related tetrapyrrole derivatives. The potential utility of these 2,2'-bipyrroles as bio-probes and ion-binding reagents are also tested.

Chapter 6 reports mechanistic studies on the unique regio-selective formation of mono-(L)-aspartylchlorin-e6. This important photodynamic therapy (PDT) photosensitizer has recently undergone a structural revision, and the work reported in this Chapter provides a rationale for the formation of the unexpected regioisomeric structure now known to belong to mono-(L)-aspartylchlorin-e6.

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