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Functionalized pi-Extended Porphyrins

Jiang, Lin
http://rave.ohiolink.edu/etdc/view?acc_num=miami1373974099

Abstract Details

2013, Doctor of Philosophy, Miami University, Chemistry and Biochemistry.
pi-Extended porphyrins are of broad interest due to their unique combination of photophysical, optoelectronic and physicochemical properties, and their potential applications in many areas. Chapter one gives general introduction to porphyrins. The description of available synthetic methods for pi-extended porphyrins is also included. In chapter two, the development of a novel synthetic methodology to synthesize opp-dibenzoporphyrins is described. A number of porphyrins with a variety of functional groups on the fused benzene rings were synthesized using this method These porphyrins were evaluated as light harvesters in dye-sensitized solar-cells (DSSCs), displaying moderate solar to electricity conversion efficiencies. Our study show that incorporation of conjugated carboxylic acid linkers on the porphyrin to further extend the conjugate system considerably broadened and red-shifted the absorption bands of the porphyrin leading to higher conversion efficiency. Chapter three is focused on the synthesis and characterization of the first examples of triphenylene-fused porphyrins through a Pd-catalyzed cascade reaction followed by oxidative ring closure. Further extension of the porphyrin pi-system to fuse one dibenzo-[fg,op]-tetracene has also been achieved using a similar approach. These pi-extended porphyrins displayed much broadened and bathochromic shifted UV-vis absorptions, as compared with their unfused precursors. In chapter four, the synthesis and characterization of highly water soluble ionic tetrabenzoporphyrins (TBPs) are presented. The UV-Vis spectra of these porphyrins displayed significantly red-shifted and broadened Soret bands. Unusually intense Q bands were observed for cationic TBPs. These interesting electronic properties have never been observed in other water soluble porphyrins. These porphyrins are substituted with eight ionic groups which are highly water soluble, and serve as potential PDT candidates. Chapter five introduces a synthetic method to prepare the pentacene-fused diporphyrin and quinone-fused dinaphtho[2,3]porphyrins. The pentacene-fused diporphyrin is remarkably more stable than the relevant pentacene and heptacene derivatives, indicating that these novel materials hold great potential for the applications in various areas. Unsymmetrical cross-conjugated quinone-fused dinaphtho[2,3]-porphyrins and triporphyrin have also been obtained using a similar approach. All these diporphyrins and triporphyrin displayed remarkably perturbed broad absorption bands spreading over the whole visible region of the spectrum, suggesting strong electronic interactions among these multichromophoric systems.
Hong Wang (Advisor)
Richard Taylor (Committee Chair)
Michael Novak (Committee Member)
Shouzhong Zou (Committee Member)
Elisabeth Widom (Committee Member)
234 p.
Materials Science; Organic Chemistry

Recommended Citations

Citations

  • Jiang, L. (2013). Functionalized pi-Extended Porphyrins [Doctoral dissertation, Miami University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=miami1373974099

    APA Style (7th edition)

  • Jiang, Lin. Functionalized pi-Extended Porphyrins. 2013. Miami University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=miami1373974099.

    MLA Style (8th edition)

  • Jiang, Lin. "Functionalized pi-Extended Porphyrins." Doctoral dissertation, Miami University, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=miami1373974099

    Chicago Manual of Style (17th edition)

miami1373974099
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© 2013, all rights reserved.
This open access ETD is published by Miami University and OhioLINK.