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Dressler, Justin J; Teraoka, Mitsuru; Espejo, Guzmán L; Kishi, Ryohei; Takamuku, Shota; Gómez-García, Carlos J; Zakharov, Lev N; Nakano, Masayoshi; Casado, Juan; Haley, Michael M
Nature chemistry, 11/2018, Letnik: 10, Številka: 11Journal Article
Many qualitative structure-property correlations between diradical character and emerging molecular properties are known. For example, the increase of diradical character further decreases the singlet-triplet energy gap. Here we show that inclusion of thiophenes within a quinoidal polycyclic hydrocarbon imparts appreciable diradical character yet retains the large singlet-triplet energy gap, a phenomenon that has no precedent in the literature. The low aromatic character of thiophene and its electron-rich nature are the key properties leading to these unique findings. A new indenoindenodibenzothiophene scaffold has been prepared and fully characterized by several spectroscopies, magnetic measurements, solid-state X-ray and state-of-the-art quantum chemical calculations, all corroborating this unique dichotomy between the diradical input and the emerging magnetic properties. New structure-property relationships such as these are not only extremely important in the field of diradical chemistry and organic electronics, but also provide new insights into the versatility of π-electron chemical bonding.
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