每周分子Molecule of the Week
Molecule of the Week: Persulfurated coronene
每周分子：过硫化六苯并苯
所有的有机化学家（以及其他许多人）都知道六苯并苯是一种高度对称的多环芳烃。它是一种非常有用的化合物，曾经有欧洲化学家决定通过增加其周围的硫原子来增加其效用。
Klaus Müllen、冯新亮和十位合作者在德累斯顿工业大学（德国）、马普高分子所（美茵兹，德国）和米兰理工大学（意大利）合成了过硫化六苯并苯并测试了它的属性（系统命名法纯正主义者将坚持称其为coroneno[1,12-cd:2,3-c′d′:4,5-c″d″:6,7-c‴d‴:8,9-c‴′d‴′:10,11-c‴″d‴″]hexakis[1,2]dithiole）。
研究人员以六苯并苯为原料，通过四步反应生成了过硫化合物：
使用AlCl3/ICl进行氯化；
用苄硫醇和碱进行硫苄化；
使用锂取代苄基；以及
在氧化条件下，用酸去除锂原子，从而形成二硫键。
这些作者们进一步获得了产物（作者们称其为“硫花”）的物理和光谱特征。由于“硫花”在普通有机溶剂中的溶解度低，因此作者们无法获得其核磁谱图或生成单晶。尽管存在这些困难，但是作者们仍然确定了整个分子是对称的六边形并且共面。
过硫化六苯并苯信息速览
CAS登记号 | 2073844-77-4 |
摩尔质量 | 673.04 g/mol |
分子式 | C24S12 |
外观 | 暗红色粉末 |
熔点 | >300 °C |
水溶性 | 不溶 |
过硫化六苯并苯危害信息
GHS分类*：这是一个新物质，其危害信息可能还不确定。 |
过硫化六苯并苯不只是实验室的珍品。“硫花”的硫含量高，氧化还原性能好，作者们预测它可以在锂硫电池的阴极上良好地工作。实验结果表明：初始放电和充电容量分别为424和496mAh/g，反映了85%的高库仑效率。这个结果以及其他结果表明，此新分子的性能优于其他含硫材料。
C&EN将过硫化六苯并苯评为2017年的年度分子之一。
【关于每周分子 】
自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社（CAS）提供的SciFinder中的CAS REGISTRY获取每周分子的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子。
All organic chemists (and many others) know coronene as a highly symmetrical polycyclic aromatic hydrocarbon. It’s quite a useful compound, and a group of European chemists decided to increase its utility by adding sulfur atoms all around its periphery.
Klaus Müllen, Xinliang Feng, and 10 coauthors at the Technical University of Dresden (Germany), the Max Planck Institute for Polymer Research (Mainz, Germany), and the Polytechnic University of Milan (Italy), synthesized and measured the properties of persulfurated coronene. (Nomenclature purists will insist on calling it coroneno[1,12-cd:2,3-c′d′:4,5-c″d″:6,7-c‴d‴:8,9-c‴′d‴′:10,11-c‴″d‴″]hexakis[1,2]dithiole.)
Beginning with coronene, the researchers produced the persulfurated compound in four steps:
chlorinating with AlCl3/ICl;
thiobenzylating with benzyl mercaptan and base;
displacing the benzyl groups with lithium; and
removing the lithium atoms with acid under oxidizing conditions to form disulfide linkages.
The authors proceeded to obtain physical and spectral properties of their product, which they call a “sulflower”. Because of the compound’s low solubility in common organic solvents, however, they were unable to obtain an NMR spectrum or to grow single crystals. Despite these difficulties, they determined that the entire molecule is symmetrically hexagonal and coplanar.
Persulfurated coronene fast facts
| CAS Reg. No. | 2073844-77-4 |
| Molar mass | 673.04 g/mol |
| Empirical formula | C24S12 |
| Appearance | Dark red powder |
| Melting point | >300 °C |
| Water solubility | Insoluble |
Persulfurated coronene hazard information
| GHS classification*: This is a new substance, and its hazards may not have been determined. |
Persulfurated coronene isn’t just a laboratory curiosity. The authors postulated that because of its high sulfur content and favorable redox behavior, their sulflower could work well in cathodes for lithium–sulfur batteries. Experimentation bore this out: Initial discharge and charge capacities of 424 and 496 mAh/g, respectively, reflected a high coulombic efficiency of 85%. This and other results showed that the performance of the new molecule compares favorably with other sulfur-based materials.
C&EN named persulfurated coronene as one of its molecules of the year for 2017.
*Globally Harmonized System of Classification and Labeling of Chemicals.
About Molecule of the Week
MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.
Copyright © 2018 American Chemical Society.
往期精选：
每周分子Molecule of the Week：α-松油醇
每周分子Molecule of the Week：L-脯氨酸
每周分子Molecule of the Week：Vismodegib
每周分子Molecule of the Week：2,5-呋喃二甲酸
长按下面二维码关注“ACS美国化学会"
更多信息，请点击"阅读原文" Learn more about this molecule.