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Bis- and mono(m-benzoic acid)-functionalized pillar[5]arenes

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Abstract

Installation of m-benzoic acid functionalities on pillar[5]arene rims resulted in bis- and mono(m-benzoic acid)-functionalized pillar[5]arenes 1 and 2. Bis(m-benzoic acid)-functionalized pillar[5]arene 1 was able to self-assemble to form one-dimensional channels with DMF molecules residing in pillar[5]arene cavities. Esterification of two carboxylic acids in 1 with decane-1,10-diol did not afford a [1]catenane, but a bicyclic compound. Although 1-decanol esterification of mono(m-benzoic acid)-functionalized pillar[5]arene 2 did not form a self-included [1]pseudorotaxane-like structure, a mono(decyl m-benzoate)-functionalized pillar[5]arene bearing an ethyl acetate chain was found to form a self-included complex with the ethyl acetate moiety residing inside the pillar[5]arene cavity.

Graphical abstract: Bis- and mono(m-benzoic acid)-functionalized pillar[5]arenes

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Publication details

The article was received on 22 Apr 2017, accepted on 15 May 2017 and first published on 15 May 2017


Article type: Paper
DOI: 10.1039/C7OB00984D
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Bis- and mono(m-benzoic acid)-functionalized pillar[5]arenes

    X. Wu, Y. Chen, W. Hu, Y. A. Liu, X. Jia, J. Li, B. Jiang and K. Wen, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00984D

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