Chemistry of Anthracene-Acetylene Oligomers XX: Synthesis, Structures, and Self-Association of Anthracene-Anthraquinone Cyclic Compounds with Ethynylene Linkers
Chemistry of Anthracene-Acetylene Oligomers XX: Synthesis, Structures, and Self-Association of Anthracene-Anthraquinone Cyclic Compounds with Ethynylene Linkers
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蒽-乙炔低聚物 XX 的化学：蒽-蒽醌环状化合物与亚乙炔连接基的合成、结构和自缔合
DOI：
10.1002/asia.201101000
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发表时间：
2011
期刊：
影响因子：
--
通讯作者：
S.
中科院分区：
文献类型：
--
作者：
Iwanaga;T.; Miyamoto;K.; Tahara;K.; Inukai;K.; Okuhata;S.; Tobe;Y.; Toyota;S.
我们通过Sonogashira偶联环化反应合成了含有一个10-取代蒽单元和一个蒽醌单元的蒽-乙炔低聚物。X射线分析显示了几乎平面的框架和由于空间位阻而导致的内部羰基部分周围的显著的平面外变形。这些化合物在溶液中发生自缔合，它们的单体-二聚体交换缔合常数通过在CDCl 3中的可变浓度1H NMR测量确定：8 mol− 1 L（10-取代基：异丙基），<5 mol− 1 L（甲氧基）和19 mol− 1 L（辛氧基）。 这些结果进行了讨论的基础上，光谱和分子轨道分析。通过STM测量观察到辛氧基化合物在液体/石墨界面处的线性分子组装。
We have synthesized anthracene–acetylene oligomers, which contained one 10‐substituted anthracene unit and one anthraquinone unit, by cyclization with Sonogashira coupling. X‐ray analysis revealed an almost‐planar framework and significant out‐of‐plane deformation around the inner carbonyl moiety because of steric hindrance. These compounds underwent self‐association in solution and their association constants for monomer–dimer exchange were determined by variable‐concentration1H NMR measurements in CDCl3: 8 mol−1L (10‐substituent: isopropyl), <5 mol−1L (methoxy), and 19 mol−1L (octyloxy). These results were discussed on the basis of spectroscopic and molecular‐orbital analysis. A linear molecular assembly of the octyloxy compound at a liquid/graphite interface was observed by STM measurements.