Janus-type BN-embedded perylene diimides via a “shuffling” strategy: Regioselective functionalizable building block towards high-performance n-type organic semiconductors

Regioselevtive functionalization of perylene diimides (PDIs) at bay area often requires multistep synthesis and strenuous recrys-tallization. Direct bromination of perylene diimides only afford the 1,6 and 1,7-regioisomers. More importantly, the 1,6-dibromo regioisomers could only be separated by preparative HPLC. Herein, we report a promising strategy for constructing Janus back-bones of BN-doped perylene diimide derivatives. This Janus-type configuration results in the unique regioselective functionalization of BN-JPDIs, which yields exclusively the 1,6-regioisomers. Further investigation shows that the Janus-type configuration leads to a net dipole moment of 1.94 D and intramolecular charge transfer, which causes substantial changes on the optoelectronic properties. Moreover, the single crystal organic field-effect transistors based on BN-JPDIs exhibit electron mobilities up to 0.57 cm2 V−1 s−1, showcasing their potential as versatile building block towards high-performance n-type organic semiconductors. Janus-type BN-embedded perylene diimides with asymmetrical insertion of B-N covalent unit were synthesized. The unique Janus configuration endows the BN-JPDIs with substantial changes on their optoelectronic properties and reactivities towards electrophiles. The electron transporting ability of BN-JPDIs was evaluated by organic field-effect transistors (OFETs), exhibiting high electron mobility up to 0.57 cm2 V−1 s−1. [Display omitted]