文摘
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The synthesis of dioxadiazuliporphyrinogen 7 and its oxidized forms: dioxadiazuliporphyrin 8 and dication82+, is reported. These compounds were characterized in solution using UV-vis and 1H and 13C NMRspectroscopic 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 thearomatic carbaporphyrinoid dication, which can be viewed as a 21,23-dicarba-22,24-dioxaporphyrin withtwo fused tropylium rings. Further insight into the geometric and magnetic manifestations of aromaticityand antiaromaticity in the case of the redox couple 8, 82+ is obtained using density functional calculationsand nucleus-independent chemical shifts.
