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Dioxadiazuliporphyrin: a near-IR redox switchable chromophore.
Autorzy
Rok wydania
2007
Czasopismo
Numer woluminu
72
Strony
9501-9509
DOI
10.1021/jo7015218
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The synthesis of dioxadiazuliporphyrinogen 7 and its oxidized forms: dioxadiazuliporphyrin 8 and dication 8(2+), is reported. These compounds were characterized in solution using UV-vis and 1H and 13C NMR spectroscopic means and in the solid state via single-crystal X-ray diffraction analysis. Dioxadiazuliporphyrin is a nonaromatic porphyrinoid, readily and reversibly oxidizable to its cation radical and to the aromatic carbaporphyrinoid dication, which can be viewed as a 21,23-dicarba-22,24-dioxaporphyrin with two fused tropylium rings. Further insight into the geometric and magnetic manifestations of aromaticity and antiaromaticity in the case of the redox couple 8, 8(2+) is obtained using density functional calculations and nucleus-independent chemical shifts.
Adres publiczny
https://doi.org/10.1021/jo7015218
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