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Helical porphyrinoids: incorporation of ferrocene subunits into macrocyclic structures.
Autorzy
Rok wydania
2008
Czasopismo
European Journal of Organic Chemistry
Strony
2601-2611
DOI
10.1002/ejoc.200800146
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Ferrocene acts as a versatile building block for the construction of porphyrinoids, providing access to macrocyclic structures of various shapes and sized. The two representative systems, shown in the figure,adopt helical conformations that undergo dynamic inversion in solution.Ferrocene‐containing porphyrinoids have been synthesized in which ferrocene‐1,1′‐diyl units are linked to a dipyrrin or thiatripyrrin to form macrocyclic structures. NMR spectroscopic evidence shows that these new systems adopt helical conformations that undergo an inversion process in solution. In addition, small amounts of unexpected scrambling products have been isolated and characterized, namely a dipyrrin‐bisferrocenophane and two expanded bis(ferrocene) macrocycles. The formation of these systems, which contain macrocyclic rings of different sizes, is a consequence of the structural flexibility of the ferrocene unit. Cyclic voltammetry shows that ferrocene oxidation is reversible in all the systems reported here, and that it is finely tuned by the properties of the ring system.
Adres publiczny
https://doi.org/10.1002/ejoc.200800146
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