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Synthesis and inclusion properties of pillar[n]arenes

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Abstract

A detailed study of the reaction conditions revealed that a quantitative cyclocondensation of 1,4-dialkoxy-2,5-bis(alkoxymethyl)-benzenes to pillar[n]arenes can be achieved by catalysis of p-toluenesulfonic acid in CH2Cl2. Major product of this new reaction is in each case a cyclopentamer (n = 5), but small amounts of the pillar[n]arenes with n = 6, 7 and 10 can be obtained as well. Different alkoxy groups in 1- and 4-position lead to regioisomers. All cyclooligomers exist in pillar structures as pair of enantiomers, which show a racemisation at room temperature, which is fast in terms of the NMR time scale. The racemisation process occurs by rotation of the 1,4-phenylene segments in the macrocyclic rings. Pillar[n]arenes exhibit novel host–guest behavior.

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Notes

  1. The parent compounds 1 6, 2 5 and 2 6 are, to our best knowledge, not known.

  2. A definite structure proof of the four regioisomers was provided by four crystal structure analyses in the case of the methoxy/n-butoxy compounds [see ref. 15]

  3. 1H and 13C NMR data are listed in Table 3.

  4. Due to the lack of symmetry, the 1H and 13C NMR signals of the five phenylene methylene subunits are strongly superimposed.

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Acknowledgments

The financial support by the National Natural Science Foundation of China (20872038, 21072064) and the Natural Science Foundation of Guangdong Province, China (06025664) is gratefully acknowledged.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, State Key Lab of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510641, China

    Yuhui Kou, Derong Cao, Hongqi Tao, Lingyun Wang, Jianquan Liang & Zhizhao Chen

  2. Institute of Organic Chemistry, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55099, Mainz, Germany

    Herbert Meier

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  1. Yuhui Kou
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  2. Derong Cao
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  3. Hongqi Tao
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  4. Lingyun Wang
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  5. Jianquan Liang
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  6. Zhizhao Chen
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  7. Herbert Meier
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Correspondence to Derong Cao or Herbert Meier.

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Kou, Y., Cao, D., Tao, H. et al. Synthesis and inclusion properties of pillar[n]arenes. J Incl Phenom Macrocycl Chem 77, 279–289 (2013). https://doi.org/10.1007/s10847-012-0242-5

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