One-Pot Synthesis of Tetraphene and Construction of Expanded Conjugated Aromatics

Acene
derivatives as a class of polycyclic aromatic hydrocarbons
have attracted considerable interest because of their outstanding
semiconductor properties. We developed a one-pot synthesis for fully
conjugated tetraphene via a sequence of propargyl-allenyl isomerization,
phosphine addition, intramolecular Wittig reactions, and Diels–Alder
cyclization reactions. The derivative-conjugated aromatic compounds
including carbazole or triphenylamine have been constructed via Pd-catalyzed
coupling reaction with dibromotetraphene. These compounds show superior
photophysical and electrochemical properties, which make them possible
candidates for optoelectronic conjugated materials.