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Isolation and Characterization of a Monoprotonated Hydroporphyrin
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.ORCID iD: 0000-0002-9450-2532
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.ORCID iD: 0000-0001-5403-9902
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.ORCID iD: 0000-0003-2449-102x
2018 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 48, p. 7051-7056Article in journal (Refereed) Published
Abstract [en]

A simple protocol for the controlled preparation of mono- and diprotonated hydroporphyrins (chlorins) is presented. The chlorins carried 10-aryl groups with electron-neutral (phenyl), electron-donating (p-OMe-C6H4) or electron-withdrawing (pentafluorophenyl) substituents. The protonation reactions were readily followed by UV/Vis absorption spectroscopy, enabling the determination of the first (4.8-5.3) and second pK(a)'s (1.7-0.5). Both mono- and diprotonated species were fully characterized by H-1 NMR spectroscopy, which, in combination with theoretical studies, showed that these macrocycles were significantly distorted in solution. A 10-phenyl-substituted monoprotonated chlorin was characterized by X-ray crystallography. This is the first structurally characterized hydroporphyrin monocation, and the first crystal structure of a sterically unencumbered singly protonated tetrapyrrole. The photostabilities of the mono- and diprotonated 10-phenylchlorins were measured upon irradiation into their Soret bands; protonation yielded increased photostabilities.

Place, publisher, year, edition, pages
2018. no 48, p. 7051-7056
Keywords [en]
Functional organic materials, Chlorin, Tetrapyrrole, Protonation, Absorption, Fluorescence
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-374119DOI: 10.1002/ejoc.201801472ISI: 000454532300027OAI: oai:DiVA.org:uu-374119DiVA, id: diva2:1281727
Funder
Swedish Research Council, 2013-4655Stiftelsen Olle Engkvist ByggmästareAvailable from: 2019-01-23 Created: 2019-01-23 Last updated: 2019-01-23Bibliographically approved

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Arkhypchuk, Anna I.Orthaber, AndreasKovacs, DanielBorbas, K. Eszter

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