Cycloparaphenylenes and Their Catenanes: Complex Macrocycles Unveiled by Ion Mobility Mass Spectrometry,Angewandte Chemie International Edition

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Cycloparaphenylenes and Their Catenanes: Complex Macrocycles Unveiled by Ion Mobility Mass Spectrometry
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2017-02-01 , DOI: 10.1002/anie.201611943
Wen Zhang ₁ , Ali Abdulkarim ₁ , Florian E. Golling _{1,

2} , Hans Joachim Räder ₁ , Klaus Müllen ₁

Affiliation

The insoluble product mixture obtained from cycloparaphenylene (CPP) synthesis from Suzuki coupling and reductive aromatization was analyzed. Traditional mass spectrometry suggests a homologous series of macrocycles with 12 to 84 phenylene units. Ion‐mobility mass spectrometry, however, unravels an unexpected complexity of isomers with identical chemical formula, but different topologies. Whereas macrocycles containing up to 30 phenylene units show only one structure, the homologue with 36 phenylene units forms at least four different isomers with significant molecular size differences. They can be assigned to catenanes composed of CPPs with 2×18 and 12+24 phenylene units together with the ordinary [36]CPP macrocycle. Most likely, a trefoil knot of the CPP with 36 moieties is also present. For the first time, catenanes can be elucidated in a simple reaction mixture by analyzing their ions in the gas phase, an analysis which lies beyond the scope of traditional analytical methods.

中文翻译：

环对亚苯基及其连环化合物：离子淌度质谱揭示的复杂大环化合物

分析了由Suzuki偶联和还原芳构化合成的环对亚苯基（CPP）获得的不溶性产物混合物。传统质谱法提出了一系列具有12至84个亚苯基单元的大环的同源序列。然而，离子迁移质谱法揭示了具有相同化学式但拓扑结构不同的异构体的意想不到的复杂性。包含多达30个亚苯基单元的大环仅显示一种结构，而具有36个亚苯基单元的同系物形成至少四个具有明显分子大小差异的不同异构体。可以将它们分配给由具有2×18和12 + 24亚苯基单元的CPP以及常规的[36] CPP大环组成的链烷烃。最有可能出现的是CPP的三叶结，共有36个部分。首次，

更新日期：2017-02-01

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