硼原子掺杂的稠环芳烃因路易斯酸性、高荧光效率、紧密的分子堆积等特征成为一类重要的光电新兴材料。可是由于合成困难，此类化合物的种类为数不多，且对于它们独特性能的研究认识不深入。本申请另辟蹊径，设计合成一系列结构新颖的硼掺杂稠环芳烃：1）双硼原子掺杂的borole类全锯齿状边缘稠环芳烃；2）单硼原子掺杂的borole类全锯齿状边缘单自由基稠环芳烃；3）硼原子掺杂的双自由基稠环芳烃。第一与第二组化合物代表稀有的borole基团嵌入的稠环芳烃，而第三组化合物则将成为首例中性的硼原子稳定双自由基稠环芳烃。由于全锯齿状边缘、近平面结构、borole引入、自由基特征、温和路易斯酸性等，这些化合物将呈现独特的光电性能、芳香性、自组装/解离、以及在路易斯碱/光/热/浓度等刺激下的构型与性能转变等。以此为基础，这类新型的硼掺杂稠环芳烃将在有机功能材料，刺激—响应性智能材料领域发挥重要作用。

Boron-doped polycyclic aromatic hydrocarbons (B-PAHs) are drawing tremendous attention in organoelectronics owing to their lewis acidity, high quantum yield, dense molecular packing mode etc. But limited examples of B-PAHs have been reported due to synthetic difficulties, let alone deeper investigation of their intriguing properties. In this proposal, we are to develop three classes of innovative B-PAHs: 1) Double-boron doped PAHs with borole subunit and all zig-zag edges; 2) Single-boron doped mono-radical PAHs with borole subunit and all zig-zag edges; 3) Boron-doped biradical PAH. Compounds of Class 1 and Class 2 are rare examples of borole-incorporated PAHs, while Class 3 stands for the first neutral boron-stablized biradical PAH. As a result of zig-zag edges, rigid planar structure, borole incorporation, radical character, mild lewis acidity etc., these compounds are bound to demonstrate unique properties: NIR abs/emission, attractive aromaticity, self-assembly/dissociation, response to external stimuli, like lewis base, light, heat, concentration and so on. Based on above inspiring properties, these newly developed B-PAHs will have wide applications in next-generation organoelectronics.