Nagase Mai, Kato Kenta, Yagi Akiko, Segawa Yasutomo, Itami Kenichiro
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602, Japan.
JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya, 464-8602, Japan.
Beilstein J Org Chem. 2020 Mar 13;16:391-397. doi: 10.3762/bjoc.16.37. eCollection 2020.
Hexa--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.
六苯并蔻（HBC）是一种难溶性多环芳烃，其直接功能化方法非常有限。本文描述了由未取代的HBC合成六硼化HBC的过程。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射线晶体学确定了六硼化HBC的晶体结构。在密度泛函理论计算的支持下，分析了所得六硼化HBC的光电性质。光谱显示，在硼基的σ供电子作用下，与未取代的HBC相比，吸收带发生了红移。
