Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes.

Beilstein Journal of Organic Chemistry
Ying HanChao-Guo Yan

Abstract

The pillar[5]arene mono- and di(oxyalkoxy)benzoic acids were successfully prepared in high yields by sequential alkylation of ω-bromoalkoxy-substituted pillar[5]arenes with methyl or ethyl p-hydroxybenzoate followed by a hydrolytic reaction under basic conditions. Under catalysis of HOBt/EDCl, the amidation reaction of pillar[5]arene mono(oxybutoxy)benzoic acid with monoamido-functionalized pillar[5]arenes afforded diamido-bridged bis-pillar[5]arenes. 1H NMR and 2D NOESY spectra clearly indicated that [1]rotaxanes were formed by insertion of longer diaminoalkylene unit into the cavity of one pillar[5]arene with another pillar[5]arene acting as a stopper. The similar catalysed amidation reaction of pillar[5]arene di(oxybutoxy)benzoic acid with monoamido-functionalized pillar[5]arenes resulted in the diamido-bridged tris-pillar[5]arenes, which successfully form the unique bis-[1]rotaxanes bearing longer than diaminopropylene diamido bridges.

References

Mar 9, 2006·Chemical Reviews·Gerhard WenzAxel Müller
Mar 29, 2007·Chemical Communications : Chem Comm·Xiang MaHe Tian
Mar 25, 2008·Journal of the American Chemical Society·Tomoki OgoshiYoshiaki Nakamoto
Nov 20, 2009·Angewandte Chemie·Derong CaoHerbert Meier
Dec 22, 2009·Chemical Society Reviews·Xiang Ma, He Tian
Feb 26, 2010·Organic Letters·Kazuhiro YamauchiAkira Harada
Feb 26, 2010·Journal of the American Chemical Society·Zheng Xue, Michael F Mayer
May 25, 2011·Chemical Communications : Chem Comm·Tomoki OgoshiTada-Aki Yamagishi
Sep 29, 2011·Chemical Communications : Chem Comm·Huacheng ZhangJ Fraser Stoddart
Jan 5, 2013·Organic & Biomolecular Chemistry·Huacheng ZhangYanli Zhao
Apr 10, 2013·Chemistry : a European Journal·Yu ChenHerbert Meier
Aug 10, 2013·ACS Nano·Huacheng ZhangYanli Zhao
Nov 20, 2013·Chemistry : a European Journal·Huacheng Zhang, Yanli Zhao
Dec 7, 2013·Chemical Communications : Chem Comm·Binyuan Xia, Min Xue
Dec 18, 2013·Accounts of Chemical Research·Albert C FahrenbachJ Fraser Stoddart
Dec 18, 2013·Chemical Communications : Chem Comm·Mengfei NiLeyong Wang
Jan 3, 2014·Organic & Biomolecular Chemistry·Yangfan GuanLeyong Wang
Apr 9, 2014·Accounts of Chemical Research·Matthew J Langton, Paul D Beer
May 9, 2014·Accounts of Chemical Research·Mingming ZhangHarry W Gibson
Jun 1, 2014·Accounts of Chemical Research·Carson J Bruns, J Fraser Stoddart
Dec 23, 2014·Chemical Communications : Chem Comm·Takahiro OgawaToshikazu Takata
Feb 24, 2015·Chemical Reviews·Da-Hui QuHe Tian
Jul 2, 2015·Nature Communications·Sheng-Hua LiYu Liu
Sep 9, 2015·Chemical Reviews·Sundus Erbas-CakmakAlina L Nussbaumer
Jun 24, 2016·Chemical Reviews·Tomoki OgoshiYoshiaki Nakamoto
Oct 8, 2016·Organic & Biomolecular Chemistry·Xie HanJun Yin
Nov 8, 2016·Chemical Communications : Chem Comm·James E M LewisStephen M Goldup
Apr 28, 2017·Chemical Society Reviews·James E M LewisStephen M Goldup
Apr 28, 2017·Chemical Communications : Chem Comm·Xu-Sheng DuYing-Wei Yang
May 4, 2017·Chemical Society Reviews·Zhichang LiuJ Fraser Stoddart
Jan 1, 2015·Chemical Science·Huanqing ChenChunju Li
May 30, 2017·Chemical Science·Yuping WangJ Fraser Stoddart
Jun 18, 2017·Journal of the American Chemical Society·Guillaume De BoDavid A Leigh
Jun 20, 2017·Journal of the American Chemical Society·Katarzyna EichstaedtThomas A Singleton
Aug 3, 2017·Chemical Communications : Chem Comm·Hendrik V SchröderChristoph A Schalley
Nov 17, 2017·Chemical Society Reviews·Derrick A RobertsJonathan R Nitschke

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Citations

Oct 5, 2021·Chemical Communications : Chem Comm·Shuang ChaoZhichao Pei

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Methods Mentioned

BETA
X-ray
amidation

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