Synthesis of BN-fused polycyclic aromatics via tandem intramolecular electrophilic arene borylation.
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[g,p]chrysene (A) and 8b,11b-diaza-19b,22b-diborahexabenzo[a,c,fg,j,l,op]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 A 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.
International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan. hatake@scl.kyoto-u.ac.jp
Takuji
T
Hatakeyama
Sigma
S
Hashimoto
Shu
S
Seki
Masaharu
M
Nakamura