Repozytorium

Dioxadiazuliporphyrin: a near-IR redox switchable chromophore.

Autorzy

Natasza Sprutta

Marta Siczek

Lechosław Latos-Grażyński

Miłosz Pawlicki

Ludmiła Szterenberg

Tadeusz Lis

Rok wydania

2007

Czasopismo

Journal of Organic Chemistry

Numer woluminu

72

Strony

9501-9509

DOI

10.1021/jo7015218

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

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

Strona internetowa wydawcy

https://www.acs.org/content/acs/en.html

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