Synthesis of Decaarylanthracene with Nine Different Substituents.

A synthesis of decaarylanthracene with nine different substituents has been accomplished by a coupling/ring-transformation strategy. The oxidation of tetraarylthiophenes with four different substituents to the corresponding thiophene S-oxides and a [4 + 2] cycloaddition with a double benzyne precursor afforded a multiply arylated naphthalene derivative. Subsequently, the naphthalene derivative was converted into a naphthalyne, and then a [4 + 2] cycloaddition of another thiophene S-oxide provided decaarylanthracenes with nine different aryl groups.