Synthesis of BN-Fused Polycyclic Aromatics via Tandem Intramolecular Electrophilic Arene Borylation

Abstract

A tandem intramolecular electrophilic arene borylation reaction has been developed for the synthesis of BN-fused polycyclic aromatic compounds such as 4b-aza-12b-boradibenzo[<i>g</i>,<i>p</i>]chrysene (<b>A</b>) and 8b,11b-diaza-19b,22b-diborahexabenzo[<i>a</i>,<i>c</i>,<i>fg</i>,<i>j</i>,<i>l</i>,<i>op</i>]tetracene. These compounds adopt a twisted conformation, which results in a tight and offset face-to-face stacking array in the solid state. Time-resolved microwave conductivity measurements prove that the intrinsic hole mobility of <b>A</b> is comparable to that of rubrene, one of the most commonly used organic semiconductors, indicating that BN-substituted PAHs are potential candidates for organic electronic materials