Palladium-Catalyzed Si-C Bond Formation toward Sila-Annulated Perylene Diimides.

The first example of sila-annulation onto the perylene diimide core that allows the effective and practical synthesis of both sila- and disilaperylene diimides (Si-PDIs and 2Si-PDIs) in one pot through palladium-catalyzed Si-C bond formation is presented. The corresponding sila-annulated perylene diimides demonstrated exceptional optical properties with noteworthy bathochromic shifts and excellent fluorescence quantum yields. Single crystal analysis revealed almost planar molecular structures and distinct packing arrangements with intense π-π interactions. Their single crystal OFET devices showed good electron mobilities of up to 0.3 cm2 V-1 s-1 under a nitrogen atmosphere.