Lu Dapeng, Wu Haotian, Dai Yafei, Shi Hong, Shao Xiang, Yang Shangfeng, Yang Jinlong, Du Pingwu
Key Laboratory of Materials for Energy Conversion, Chinese Academy of Sciences, Department of Materials Science and Engineering, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), University of Science and Technology of China (USTC), 96 Jinzhai Road, Hefei, Anhui Province 230026, P. R. China.
Chem Commun (Camb). 2016 Jun 4;52(44):7164-7. doi: 10.1039/c6cc03002e. Epub 2016 May 13.
Herein we report the synthesis of a novel hexabenzocoronene-containing cycloparaphenylene carbon nanoring, cyclo[12]-paraphenylene[2]-2,11-hexabenzocoronenylene, by metal-mediated cross-coupling reactions. The nanoring was accomplished by rationally designed palladium-catalyzed coupling of diborylhexabenzocoronene and L-shaped cyclohexane units, followed by nickel-mediated C-Br/C-Br coupling and the aromatization of cyclohexane moieties. The structure was confirmed by NMR and HR-MS. Especially, the cycloparaphenylene structure is firstly observed by STM. The photophysical properties were studied using UV-Vis spectroscopy, photoluminescence (PL) spectroscopy, and theoretical calculations.
在此,我们报道了通过金属介导的交叉偶联反应合成一种新型含六苯并蔻的环对亚苯基碳纳米环,即环[12]-对亚苯基[2]-2,11-六苯并蔻烯基。该纳米环是通过合理设计的钯催化二硼基六苯并蔻与L形环己烷单元的偶联反应,随后进行镍介导的C-Br/C-Br偶联以及环己烷部分的芳构化反应而制备的。其结构通过核磁共振(NMR)和高分辨质谱(HR-MS)得以确认。特别地,通过扫描隧道显微镜(STM)首次观察到了环对亚苯基结构。利用紫外可见光谱、光致发光(PL)光谱以及理论计算对其光物理性质进行了研究。