Synthesis of Boron-Doped Polycyclic Aromatic Hydrocarbons by Tandem Intramolecular Electrophilic Arene Borylation,Organic Letters

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Synthesis of Boron-Doped Polycyclic Aromatic Hydrocarbons by Tandem Intramolecular Electrophilic Arene Borylation
Organic Letters ( IF 4.9 ) Pub Date : 2015-11-25 00:00:00 , DOI: 10.1021/acs.orglett.5b03167
Fumiya Miyamoto ₁ , Soichiro Nakatsuka ₁ , Keitaro Yamada ₂ , Ken-ichi Nakayama ₂ , Takuji Hatakeyama _{1,

3}

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Tandem intramolecular electrophilic arene borylation was developed to facilitate access to B-doped polycyclic aromatic hydrocarbons (PAHs). DFT calculations revealed that electrophilic arene borylation occurred via a four-membered ring transition state, in which C–B and H–Br bonds formed in a concerted manner. An organic light-emitting diode employing the B-doped PAH as an emitter and a B-doped PAH-based field-effect transistor were successfully fabricated, demonstrating the potential of B-doped PAHs in materials science.

中文翻译：

串联分子内亲电芳烃硼化反应合成掺硼多环芳烃

开发了串联分子内亲电芳烃硼酸酯化反应以促进获得B掺杂的多环芳烃（PAH）。DFT计算表明，亲电芳烃的硼化反应是通过四元环跃迁状态发生的，其中C-B和H-Br键以协调的方式形成。成功地制造了将B掺杂的PAH用作发射极的有机发光二极管和基于B掺杂的PAH的场效应晶体管，证明了B掺杂的PAH在材料科学中的潜力。

更新日期：2015-11-25

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