Octaiodoporphyrin and Octaiodocorrole: Isolation of a Cis Porphyrin Tautomer

Thomassen, Ivar Kristian

dc.contributor.advisor	Ghosh, Abhik
dc.contributor.author	Thomassen, Ivar Kristian
dc.date.accessioned	2018-09-06T12:18:26Z
dc.date.available	2018-09-06T12:18:26Z
dc.date.issued	2018-09-28
dc.description.abstract	Iodinated aromatics are excellent starting materials for further elaboration via transition-metal-catalyzed cross-coupling reactions. Considering the diverse applications of porphyrins and corroles - as photosensitizers in photodynamic therapy, dye sensitized solar cells, near-infrared dyes, gas sensors, nonlinear optical materials, and catalysts - the synthetic potential of β-polyiodinated or octaiodinated porphyrins and corroles may be considerable. As part of my doctoral studies, I have synthesized and structurally characterized the first examples of both β-octaiodinated porphyrins and β-octaiodinated corroles. Furthermore, a single-crystal X-ray structure of free base β-octaiodoporphyrin provided an example of a cis porphyrin tautomer, the long hypothesized intermediate of porphyrin NH tautomerism.	en_US
dc.description.doctoraltype	ph.d.	en_US
dc.description.popularabstract	Porphyrins are a class of ring-shaped molecules capable of binding a metal ion at their center, which are perhaps most familiar in the form of the red color (hemoglobin) of blood and the green color (chlorophyll) of plants. They serve an incredible number of biological functions and are often referred to as the colors of life. Chemists are adept at making synthetic analogues of these molecules, which can also be very useful in a wide-range of applications such as cancer treatment, the construction of solar cells, and industrial catalysis. This is what I have worked on. The synthetic porphyrins that I have made should act as precursors to a variety of reagents for cancer imaging and therapy. In a second development, I have studied in depth the position and movement of the hydrogen atoms in a metal-free porphyrin. This study should allow a deeper understanding of how porphyrins incorporate a metal such as iron when forming hemoglobin.	en_US
dc.description.sponsorship	I wish to thank the Research Council of Norway’s FRIPRO program for supporting me and giving me the freedom to pursue my own ideas.	en_US
dc.description	<p>Paper A and paper B with supporting information are not available in Munin. <p> <p>Paper A: Thomassen, I.K., Vazquez-Lima, H., Gagnon, K.J. & Ghosh, A. (2015). Octaiodoporphyrin. Available in <a href=https://doi.org/10.1021/acs.inorgchem.5b02127>Inorganic Chemistry, 54(23), 11493-11497.</a><p> <p>Paper B: Thomassen, I.K., McCormick, L.J & Ghosh, A. (2018). Molecular Structure of a β-Octaiodo-meso-tetraarylporphyrin. A Rational Route to cis Porphyrin Tautomers? (Manuscript). Published version, with altered title, available in <a href=https://doi.org/10.1021/acs.cgd.8b00629>Crystal Growth & Design, 18(8), 4257-4259.</a><p>	en_US
dc.identifier.isbn	978-82-8236-314-3 (trykt) og 978-82-8236-315-0 (pdf)
dc.identifier.uri	https://hdl.handle.net/10037/13701
dc.language.iso	eng	en_US
dc.publisher	UiT Norges arktiske universitet	en_US
dc.publisher	UiT The Arctic University of Norway	en_US
dc.rights.accessRights	openAccess	en_US
dc.rights.holder	Copyright 2018 The Author(s)
dc.rights.uri	https://creativecommons.org/licenses/by-nc-sa/3.0	en_US
dc.rights	Attribution-NonCommercial-ShareAlike 3.0 Unported (CC BY-NC-SA 3.0)	en_US
dc.subject	VDP::Mathematics and natural science: 400::Chemistry: 440::Inorganic chemistry: 442	en_US
dc.subject	VDP::Matematikk og Naturvitenskap: 400::Kjemi: 440::Uorganisk kjemi: 442	en_US
dc.title	Octaiodoporphyrin and Octaiodocorrole: Isolation of a Cis Porphyrin Tautomer	en_US
dc.type	Doctoral thesis	en_US
dc.type	Doktorgradsavhandling	en_US