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Title
Japanese: 
English:Hexathioalkyl sumanenes: An electron-donating buckybowl as a building block for supramolecular materials 
Author
Japanese: 庄子 良晃, 梶谷 孝, 石割 文崇, DING Qiang, H. Sato, H. Anetai, T. Akutagawa, 櫻井 英博, 福島 孝典.  
English: Y. Shoji, T. Kajitani, F. Ishiwari, Q. Ding, H. Sato, H. Anetai, T. Akutagawa, H. Sakurai, T. Fukushima.  
Language English 
Journal/Book name
Japanese: 
English:Chemical Science 
Volume, Number, Page Vol. 8    Issue 12    Page 8405–8410
Published date Oct. 18, 2017 
Publisher
Japanese: 
English: 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL https://pubs.rsc.org/en/content/articlelanding/2017/sc/c7sc03860g#!divAbstract
 
DOI https://doi.org/10.1039/C7SC03860G
Abstract Unlike planar aromatic compounds, bowl-shaped sumanene, which has concave and convex faces with different electrostatic potentials, tends to form a one-dimensional columnar assembly without causing slip-stacking in the crystal. Here we report the first successful synthesis of liquid-crystalline (LC) sumanenes, which was brought about by the incorporation of six thioalkyl groups (R = SC6H13 or SC12H25) into the aromatic part of sumanene. In contrast to the case of the mesophase formation of corannulene, which requires the presence of many dendritic side chains, sumanene derivatives with simple alkyl chains can exhibit a remarkably high-order columnar LC mesophase over a wide temperature range. While non-substituted sumanene inherently behaves as an electron acceptor, hexathioalkyl versions, such as hexathiomethyl sumanene, show electron-donating properties, resulting in complexation with C60. Considering its unique shape, electronic properties, and self-assembly behavior, the electron-donating sumanene may represent a new building block for constructing supramolecular materials, both by itself and in combination with fullerene derivatives.

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