Effect of Alkylpyrazinium Counterions on the Host-guest Recognition Based on Dimethoxypillar[5]arenes

doi:10.1007/s40242-016-5402-5

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (2): 202-206.doi: 10.1007/s40242-016-5402-5

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Effect of Alkylpyrazinium Counterions on the Host-guest Recognition Based on Dimethoxypillar[5]arenes

LIU Lijing, GUO Lei, ZHAO Qiuhua, SHAN Yongkui, LIAO Xiaojuan

School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241, P. R. China

Received:2015-10-19 Revised:2015-11-06 Online:2016-04-01 Published:2015-12-14
Contact: LIAO Xiaojuan E-mail:xjliao@chem.ecnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21204022), the Research Fund for the Doctoral Program of Higher Education of China(No.20120076120005), the Fundamental Research Funds for the Central Universities of China and the Large Instruments Open Fundation of East China Normal University, China(No.201409251425).

Abstract

Abstract:

In this work, we synthesized n-octylpyrazinium bromide(G-Br) and n-octylpyrazinium hexafluorophosphate(G-PF₆) as model guests and studied their host-guest complexation with 1,4-dimethoxypillar[5]arene(DMP5A). Effect of alkylpyrazinium counterions on the host-guest recognition was investigated. Based on the ¹H NOESY spectra, the binding site of DMP5A with G-PF₆ is the same as that of DMP5A with G-Br. However, G-PF₆ forms a stronger complex with DMP5A than G-Br, owing to that hexafluorophosphate forms weaker doubly inonic H-bonds with ammonium cation than bromide ion in chloroform, which leads to some aggregates that could be dissociated with the addition of DMP5A.

Key words: Pillararene, Counterion, Host-guest recognition, Supramolecular chemistry

LIU Lijing, GUO Lei, ZHAO Qiuhua, SHAN Yongkui, LIAO Xiaojuan. Effect of Alkylpyrazinium Counterions on the Host-guest Recognition Based on Dimethoxypillar[5]arenes[J]. Chemical Research in Chinese Universities, 2016, 32(2): 202-206.

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Effect of Alkylpyrazinium Counterions on the Host-guest Recognition Based on Dimethoxypillar[5]arenes

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