Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility
Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility
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二苯并二氮杂吡啶：具有高载流子迁移率的双 N 掺杂环戊稠合多环分子
DOI：
10.1002/anie.202200341
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发表时间：
2022
期刊：
影响因子：
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通讯作者：
Tanaka Takayuki
中科院分区：
文献类型：
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作者：
Morimoto Yuki;Koo Yun Hee;Otsubo Kazuya;Kitakado Hidetsugu;Seki Shu;Osuka Atsuhiro;Tanaka Takayuki
吡并苯是一种独特的环戊稠合多环芳烃（CP-PAH），具有双重芳香特性。本文中，我们报道了通过[2.2]（2，5）吡咯烷型前体的氧化N-N连接反应合成双N掺杂的苯并环化的吡喃，即二苯并二氮杂吡喃。二苯并二氮杂吡喃类化合物在固态下表现出良好的有序π堆叠分子堆积，这对于沿着堆叠方向的有效空穴传输是可行的。高载流子迁移率估计微波电导率测量相比，二苯并噻嗪。通过电化学方法验证了二苯并二氮杂并吡喃的高HOMO能级，并检测到了其持久的自由基阳离子物种。
Pyracylene is a unique cyclopenta‐fused polycyclic aromatic hydrocarbon (CP‐PAH) that exhibits dual aromatic characteristics. Herein we report the synthesis of doubly N‐doped benzannulated pyracylenes, namely dibenzodiazapyracylenes, by oxidative N−N linking reaction of [2.2](2,5)pyrrolophane‐type precursors. Dibenzodiazapyracylenes displayed well‐ordered π‐stacked molecular packing in the solid state, which were feasible for effective hole‐transporting along the stacking direction. High carrier mobility was estimated by microwave conductivity measurements as compared to dibenzoullazine. The high HOMO level of dibenzodiazapyracylene was verified by electrochemistry and its persistent radical cation species has been detected.