Dioxadiazuliporphyrin: a near-IR redox switchable chromophore |
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Authors: | Sprutta Natasza Siczek Marta Latos-Grazyński Lechos?aw Pawlicki Mi?osz Szterenberg Ludmi?a Lis Tadeusz |
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Institution: | Department of Chemistry, University of Wroc?aw, 14 F. Joliot-Curie Street, Wroc?aw 50 383, Poland. |
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Abstract: | 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. |
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