Effect of alkylpyrazinium counterions on the host-guest recognition based on dimethoxypillar[5]arenes

Lijing Liu; Lei Guo; Qiuhua Zhao; Yongkui Shan; Xiaojuan Liao

doi:10.1007/s40242-016-5402-5

Effect of alkylpyrazinium counterions on the host-guest recognition based on dimethoxypillar[5]arenes

Lijing Liu
, Lei Guo
, Qiuhua Zhao
, Yongkui Shan
, Xiaojuan Liao^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

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.

Original language	English
Pages (from-to)	202-206
Number of pages	5
Journal	Chemical Research in Chinese Universities
Volume	32
Issue number	2
DOIs	https://doi.org/10.1007/s40242-016-5402-5
State	Published - 1 Apr 2016

Keywords

Counterion
Host-guest recognition
Pillararene
Supramolecular chemistry

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10.1007/s40242-016-5402-5

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@article{978bb0081424435f810d4e82f150cae8,

title = "Effect of alkylpyrazinium counterions on the host-guest recognition based on dimethoxypillar[5]arenes",

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.",

keywords = "Counterion, Host-guest recognition, Pillararene, Supramolecular chemistry",

author = "Lijing Liu and Lei Guo and Qiuhua Zhao and Yongkui Shan and Xiaojuan Liao",

note = "Publisher Copyright: {\textcopyright} 2016, Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH.",

year = "2016",

month = apr,

day = "1",

doi = "10.1007/s40242-016-5402-5",

language = "英语",

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pages = "202--206",

journal = "Chemical Research in Chinese Universities",

issn = "1005-9040",

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TY - JOUR

T1 - Effect of alkylpyrazinium counterions on the host-guest recognition based on dimethoxypillar[5]arenes

AU - Liu, Lijing

AU - Guo, Lei

AU - Zhao, Qiuhua

AU - Shan, Yongkui

AU - Liao, Xiaojuan

PY - 2016/4/1

Y1 - 2016/4/1

N2 - 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.

AB - 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.

KW - Counterion

KW - Host-guest recognition

KW - Pillararene

KW - Supramolecular chemistry

UR - https://www.scopus.com/pages/publications/84963772463

U2 - 10.1007/s40242-016-5402-5

DO - 10.1007/s40242-016-5402-5

M3 - 文章

AN - SCOPUS:84963772463

SN - 1005-9040

VL - 32

SP - 202

EP - 206

JO - Chemical Research in Chinese Universities

JF - Chemical Research in Chinese Universities

IS - 2

ER -

Effect of alkylpyrazinium counterions on the host-guest recognition based on dimethoxypillar[5]arenes

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Keywords

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