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.