International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
J Am Chem Soc. 2011 Nov 23;133(46):18614-7. doi: 10.1021/ja208950c. Epub 2011 Oct 31.
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.
发展了一种串联分子内亲电芳基硼化反应，用于合成 BN 稠合多环芳烃化合物，如 4b-氮杂-12b-硼二苯并[g,p]苝（A）和 8b,11b-二氮杂-19b,22b-二硼六苯并[a,c,fg,j,l,op]四烯。这些化合物采用扭曲构象，导致在固态中形成紧密且交错的面对面堆积排列。时间分辨微波电导率测量证明，A 的本征空穴迁移率可与最常用的有机半导体之一芴的迁移率相媲美，这表明 BN 取代的 PAHs 是有机电子材料的潜在候选者。
