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Pyrazinoporphyrins: Expanding a Pyrrolic Building Block in meso‐Tetraphenylporphyrin by a Nitrogen Atom
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Titel: |
Pyrazinoporphyrins: Expanding a Pyrrolic Building Block in meso‐Tetraphenylporphyrin by a Nitrogen Atom |
In: | European Journal of Organic Chemistry, 2016, 2016, 5, S. 992-998 |
veröffentlicht: |
Wiley
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Umfang: | 992-998 |
ISSN: |
1099-0690 1434-193X |
DOI: | 10.1002/ejoc.201501436 |
Zusammenfassung: | <jats:title>Abstract</jats:title><jats:p>Application of a variant of our “porphyrin breaking and mending strategy” to free base and Ni<jats:sup>II</jats:sup> complexes of <jats:italic>meso</jats:italic>‐tetraarylporphyrin – dihydroxylation, oxidative diol cleavage and reaction of the resulting <jats:italic>seco</jats:italic>‐chlorin bis(aldehyde) with ammonia – generates pyrazinoporphyrins. Thus, a nitrogen atom was inserted between the two former β‐carbon atoms, overall formally replacing a pyrrolic building block by a pyrazine moiety. Treatment of the initially formed pyrazine hemiaminals with alcohols converts them into the corresponding hemiaminal ethers. This stabilizes the chromophores significantly, but the free‐base pyrazinoporphyrins still remain sensitive toward (acid‐induced) degradation reactions. Free‐base pyrazinoporphyrins possess slightly redshifted porphyrin‐type UV/Vis spectra, while the spectra of the pyrazinoporphyrin Ni<jats:sup>II</jats:sup> complexes resemble more those of metallochlorins.</jats:p> |
Format: | E-Article |
Quelle: | Wiley (CrossRef) |
Sprache: | Englisch |