Synthesis, Characterization, and Properties of BN-Fluoranthenes,Organic Letters

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Synthesis, Characterization, and Properties of BN-Fluoranthenes
Organic Letters ( IF 4.9 ) Pub Date : 2022-06-22 , DOI: 10.1021/acs.orglett.2c01342
Erlong Li ₁ , Mengjia Jin ₂ , Ruijun Jiang ₁ , Lei Zhang ₃ , Yanli Zhang ₁ , Meiyan Liu ₁ , Xiaoming Wu ₂ , Xuguang Liu _{1,

4}

Affiliation

Boron/nitrogen-doped fluoranthenes, a new class of BN-doped cyclopenta-fused polycyclic aromatic hydrocarbons, were synthesized via pyrrolic-type nitrogen directed C–H borylation. Regioselective bromination of BN-fluoranthene (3a) gave mono- and dibrominated BN-fluoranthenes. The halogenated BN-fluoranthene (3b) can undergo various of further cross-coupling reactions to deliver a series of BN-fluoranthenes. Moreover, incorporating BN unit in to fluoranthene resulted in a wider HOMO–LUMO energy gaps. The aromaticities of the BN-fluoranthene (3a) were quantified by experimental and computational studies.

中文翻译：

BN-荧蒽的合成、表征和性质

硼/氮掺杂荧蒽是一类新的 BN 掺杂环戊稠合多环芳烃，通过吡咯型氮定向 C-H 硼化反应合成。BN-荧蒽的区域选择性溴化 ( 3a ) 得到单溴化和二溴化的 BN-荧蒽。卤化的BN-荧蒽( 3b )可以进行各种进一步的交叉偶联反应以产生一系列BN-荧蒽。此外，将BN单元结合到荧蒽中会导致更宽的HOMO-LUMO能隙。BN-荧蒽 ( 3a ) 的芳香性通过实验和计算研究进行量化。

更新日期：2022-06-22

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