Scalable synthesis of [8]cycloparaphenyleneacetylene carbon nanohoop using alkyne metathesis
Scalable synthesis of [8]cycloparaphenyleneacetylene carbon nanohoop using alkyne metathesis
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使用炔复分解法大规模合成[8]环对苯乙炔碳纳米环
DOI：
10.1039/d1cc04776k
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发表时间：
2021
影响因子：
4.9
通讯作者：
Lee, Semin
中科院分区：
文献类型：
--
作者：
Zhou, Xin;Kwon, Hyejin;Thompson, Richard R.;Herman, Robert J.;Fronczek, Frank R.;Bruns, Carson J.;Lee, Semin
大规模合成环对苯乙炔一直是具有挑战性的，由于低的大环化产率和苛刻的芳构化方法，往往分解紧张的炔。在本文中，使顺式-芪基结构单元经受炔复分解大环化。烯烃选择性溴化和脱溴化氢的以下顺序以高收率提供具有良好可扩展性的[8]环对亚苯基乙炔衍生物。X射线晶体结构和计算分析揭示了纳米环上的八个甲基的独特的同边构象。
Large scale synthesis of cycloparaphenyleneacetylenes has been challenging due to low macrocyclization yields and harsh aromatization methods that often decompose strained alkynes. Herein, a cis-stilbene-based building block is subjected to alkyne metathesis macrocylization. The following sequence of alkene-selective bromination and dehydrobromination afforded a [8]cycloparaphenyleneacetylene derivative in high yield with good scalability. X-Ray crystal structure and computational analysis revealed a unique same-rim conformation for the eight methyl groups on the nanohoop.