Two-Step Synthesis of Boron-Fused Double Helicenes
Two-Step Synthesis of Boron-Fused Double Helicenes
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DOI：
10.1021/jacs.6b01674
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发表时间：
2016-04-27
影响因子：
15
通讯作者：
Hatakeyama, Takuji
中科院分区：
文献类型：
--
作者：
Katayama, Takazumi;Nakatsuka, Soichiro;Hatakeyama, Takuji
以六溴苯为原料，通过哈特反应和脱甲基环化反应两步合成了新型硼稠合双[5]螺烯。母螺烯表现出优异的双极导电性，这可以通过独特的3D π堆叠与砖砌结构来解释。此外，四个叔丁基的引入抑制了外消旋化，从而实现光学拆分。对映体纯的螺烯显示深蓝色荧光，Commission Internationale de l'Eclairage坐标为（0.15，0.08），具有圆偏振发光活性。
Novel boron-fused double [5]helicenes were synthesized from hexabromobenzene in two steps via Hart reaction and demethylative cyclization. The parent helicene shows excellent ambipolar conductivity, which can be explained by unique 3D pi-stacking with a brickwork arrangement. Moreover, the introduction of four tert-butyl groups suppresses racemization, enabling optical resolution. The enantiomerically pure helicene shows deep blue fluorescence with Commission Internationale de l'Eclairage coordinates of (0.15, 0.08) and circularly polarized luminescence activity.