Six-fold C–H borylation of hexa-peri-hexabenzocoronene,Beilstein Journal of Organic Chemistry

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Six-fold C–H borylation of hexa-peri-hexabenzocoronene
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-03-13 , DOI: 10.3762/bjoc.16.37
Mai Nagase ₁ , Kenta Kato ₁ , Akiko Yagi ₁ , Yasutomo Segawa _{1,

2} , Kenichiro Itami _{1,

2,

3}

Affiliation

Hexa-peri-hexabenzocoronene (HBC) is known to be a poorly soluble polycyclic aromatic hydrocarbon for which direct functionalization methods have been very limited. Herein, the synthesis of hexaborylated HBC from unsubstituted HBC is described. Iridium-catalyzed six-fold C–H borylation of HBC was successfully achieved by screening solvents. The crystal structure of hexaborylated HBC was confirmed via X-ray crystallography. Optoelectronic properties of the thus-obtained hexaborylated HBC were analyzed with the support of density functional theory calculations. The spectra revealed a bathochromic shift of absorption bands compared with unsubstituted HBC under the effect of the σ-donation of boryl groups.

中文翻译：

六-六苯并六苯并六重C-H硼化

已知六六苯并晕烯（HBC）是一种难溶性多环芳烃，其直接官能化方法非常有限。本文描述了从未取代的 HBC 合成六硼化 HBC。通过筛选溶剂，成功实现了铱催化的 HBC 六重 C-H 硼化反应。通过 X 射线晶体学证实了六硼化 HBC 的晶体结构。在密度泛函理论计算的支持下分析了由此获得的六硼化HBC的光电性质。与未取代的 HBC 相比，在硼基基团 σ 供体的影响下，光谱显示吸收带发生红移。

更新日期：2020-03-16

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