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Isolation and Chara...
Isolation and Characterization of a Monoprotonated Hydroporphyrin
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- Arkhypchuk, Anna I. (author)
- Uppsala universitet,Molekylär biomimetik
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- Orthaber, Andreas, 1979- (author)
- Uppsala universitet,Molekylär biomimetik
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- Kovacs, Daniel (author)
- Uppsala universitet,Molekylär biomimetik
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- Borbas, K. Eszter (author)
- Uppsala universitet,Molekylär biomimetik
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(creator_code:org_t)
- 2018-12-06
- 2018
- English.
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In: European Journal of Organic Chemistry. - : Wiley. - 1434-193X .- 1099-0690. ; :48, s. 7051-7056
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- Functional organic materials
- Chlorin
- Tetrapyrrole
- Protonation
- Absorption
- Fluorescence
Publication and Content Type
- ref (subject category)
- art (subject category)
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