Synthesis and Characterization of [5]Cycloparaphenylene

详细信息    查看全文

• 作者：Eiichi Kayahara ; Vijay Kumar Patel ; Shigeru Yamago
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：February 12, 2014
• 年：2014
• 卷：136
• 期：6
• 页码：2284-2287
• 全文大小：267K
• ISSN：1520-5126

文摘

The synthesis of highly strained [5]cycloparaphenylene ([5]CPP), a structural unit of the periphery of C₆₀ and the shortest possible structural constituent of the sidewall of a (5,5) carbon nanotube, was achieved in nine steps in 17% overall yield. The synthesis relied on metal-mediated ring closure of a triethylsilyl (TES)-protected masked precursor 1c followed by removal of the TES groups and subsequent reductive aromatization. UV鈥搗is and electrochemical studies revealed that the HOMO鈥揕UMO gap of [5]CPP is narrow and is comparable to that of C₆₀, as predicted by theoretical calculations. The results suggest that [5]CPP should be an excellent lead compound for molecular electronics.