Abstract
A series of novel tetrasubstituted dipyranylidenes (DIPO) consisting of large π-extended moieties located at the four edge of the quinoidal core were synthesized and characterized with UV–visible, photoluminescence spectroscopies and cyclic voltammetry. Tetraphenyldipyranylidene compound has a high molar absorption coefficient with ε = 8.73 × 104 l/mol.cm at 456 nm. Larger π-extended DIPO derivatives show a bathochromic absorption peak with lower molar absorption coefficient. In the presence of large π-extended moieties, these molecules present a higher first oxidation potential, leading to a deeper HOMO level. Remarkably, naphthyl, benzothienyl and benzofuryl-substituted DIPO show a third oxidation potential at 0.91 V, 0.99 V and 1.08 V respectively. These novel compounds which combined both aromatic and quinoidal characters are attractive for their applications as multiredox active materials.
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