首页|Thienothiophene-centered ladder-type π-systems that feature distinct quinoidal π-extension
Thienothiophene-centered ladder-type π-systems that feature distinct quinoidal π-extension
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Quinoidal π-conjugated structures,a kind of fundamental subunits for organic π-systems,may produce some intriguing optical,electronic and magnetic properties of polycyclic hydrocarbons(PHs).Herein,we report two thienothiophene-centered ladder-type polycyclic molecules(1 and 2),which possess one quinoidal thienothiophene moiety and two para-quinodimethane(p-QDM)subunits,respectively.As theoretically and experimentally studied,while 1 is a fully closed-shell molecule,2 owns an open-shell structure along with partial contribution of tetraradical state that is induced by the resonance of p-QDM.Moreover,although 2 has a larger π-conjugated skeleton and open-shell electronic state,it exhibits larger bandgap and blue-shifted absorption.On the other hand,the reversible oxidation activity of 1 enables the preparation of its dication 12+,and the studies on its single-crystal and aromatic structures demonstrate that its two positive charges are delocalized onto the oxygen atoms,thus achieving fullyπ-extended structure and near-infrared absorption.This study not only gains insight into quinoidal 7r-subunits,but also provides an important basis for the development of antiaromatic and open-shellπ-electron materials.
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