From a 1,2-azaborinine to large BN-PAHs via electrophilic cyclization: synthesis, characterization and promising optical properties
From a 1,2-azaborinine to large BN-PAHs via electrophilic cyclization: synthesis, characterization and promising optical properties
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DOI：
10.1039/d0qo00723d
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发表时间：
2021-01-07
影响因子：
5.4
通讯作者：
Staubitz, Anne
中科院分区：
文献类型：
--
作者：
Appiarius, Yannik;Stauch, Tim;Staubitz, Anne
我们提出了一个收敛的合成路线对含硼氮多环芳烃（BN-PAH），使我们能够合成六个衍生物。从1，2-氮杂硼杂环庚三烯亲核试剂和各种芳基亲电试剂的结合开始，关键步骤是通过各自的炔前体的亲电环闭合来延伸芳族体系。我们的路线允许使用取代的PAH前体被规避，这往往是不可用的。相反，它只从容易获得的单核细胞中积累BN-PAH。所有衍生物在溶液和固态中发射，量子产率高达Φ（lum）= 0.40和小斯托克斯位移。固态下的发射波长明显依赖于环的连通性。由于在一个衍生物的激基缔合物的形成，其发射显着红移与一个相对缓慢的二次光致发光（PL）衰减。
We present a convergent synthetic route towards boron-nitrogen containing polycyclic aromatic hydrocarbons (BN-PAHs) that allowed us to synthesize six derivatives. Starting from the conjunction of a 1,2-azaborinine nucleophile and various aryl electrophiles, the key step was the extension of the aromatic system via an electrophilic ring closure of the respective alkyne precursors. Our route allows the use of substituted PAH precursors to be circumvented, which are often unavailable. Instead, it builds up the BN-PAHs solely from easily accessible monocycles. All derivatives were emissive in solution and solid state with quantum yields up to Phi(lum) = 0.40 and small Stokes shifts. The emission wavelengths in solid state were notably dependent on the connectivity of the rings. Due to excimer formation in one derivative, its emission was significantly redshifted with a comparatively slow secondary photoluminescence (PL) decay.