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Synthesis of Ligands and Macrocycles Based on 1,3-Diiminoisoindoline and Study of New Highly Fluorescent and Symmetric Pyrrole-BF2 Chromophores

Tamgho, Ingrid-Suzy
http://rave.ohiolink.edu/etdc/view?acc_num=akron1412163224

Abstract Details

2014, Doctor of Philosophy, University of Akron, Chemistry.
Discovered in 1907 by Braun and Tcherniac, a phthalocyanine is a macrocycle composed of four isoindolines. The metal chemistry of this macrocycle is rich, as of today, the phthalocyanines are well-known dyes and photosensitizers. Among the variety of phthalocyanine precursors, 1,3-diiminoisoindoline and phthalonitrile are the most widely used. Indeed, new macrocyles and ligands are synthesized from these compounds, either by condensation of 1,3-diiminoisoindoline or the CaCl2-catalyzed reaction of phthalonitrile with an amine. Following these methods, we are able to prepare a series of compounds, the phthalocrown, and also revisit the chemistry of bis(alkylimino)isoindolines. The first part of the dissertation describes the synthesis and characterization of phthalocrowns. They can be considered as chimera molecules composed of a crown ether and phthalocyanine. These compounds are synthesized via Schiff base-type condensation reactions between polyetherdiamines and 1,3-diiminoisoindoline, which can be generated from phthalonitrile. Secondly, we revisit the chemistry of bis(alkylimino)isoindolines. These compounds can be generated via phthalonitrile and 1,3-diiminoisoindoline depending on the nature of the amine. Also, the metal chemistry of these compounds with Ag(I) is described. One important class of fluorescent dyes is known as BODIPY. This fluorophore consists of a dipyrromethene bound to a central BF2 unit. The compound is found to possess excellent photophysical properties such as high extinction coefficient and high quantum yield of emission. Moreover, BODIPY is insensitive to pH and solvent polarity and is photostable. Its versatility, introduced via the attachment of biomolecules or other moieties, allows these dyes to have important applications from biological imaging and sensing to light harvesting. In the final chapter, we discuss the synthesis of a novel family of fluorophores, the BOPHY. These dyes are synthesized via the Schiff-base reaction of a pyrrole carbaldehyde with hydrazine, followed with a BF2 complexation to yield highly fluorescent chromophores. The BOPHY optical properties are discussed in the final chapter as well.
Christopher Ziegler, Dr (Advisor)
Claire Tessier, Dr (Committee Member)
Michael Taschner, Dr (Committee Member)
Yi Pang, Dr (Committee Member)
Kevin Cavicchi, Dr (Committee Member)
186 p.
Chemistry
phthalocyanine, DII, schiff bases, bodipy, bophy, fluorophores, isoindolines, N-heterocycle,

Recommended Citations

Citations

  • Tamgho, I.-S. (2014). Synthesis of Ligands and Macrocycles Based on 1,3-Diiminoisoindoline and Study of New Highly Fluorescent and Symmetric Pyrrole-BF2 Chromophores [Doctoral dissertation, University of Akron]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=akron1412163224

    APA Style (7th edition)

  • Tamgho, Ingrid-Suzy. Synthesis of Ligands and Macrocycles Based on 1,3-Diiminoisoindoline and Study of New Highly Fluorescent and Symmetric Pyrrole-BF2 Chromophores. 2014. University of Akron, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=akron1412163224.

    MLA Style (8th edition)

  • Tamgho, Ingrid-Suzy. "Synthesis of Ligands and Macrocycles Based on 1,3-Diiminoisoindoline and Study of New Highly Fluorescent and Symmetric Pyrrole-BF2 Chromophores." Doctoral dissertation, University of Akron, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=akron1412163224

    Chicago Manual of Style (17th edition)

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This open access ETD is published by University of Akron and OhioLINK.