Organic Letters
Organic Letters
5 years ago

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

Palladium-Catalyzed Si–C Bond Formation toward Sila-Annulated Perylene Diimides
Wei Jiang, Chunming Liu, Dong Meng, Zhaohui Wang, Chengyi Xiao, Zetong Ma
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02011

DOI: 10.1021/acs.orglett.7b02011

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