Synthesis and inclusion properties of pillar[n]arenes |
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Authors: | Yuhui Kou Derong Cao Hongqi Tao Lingyun Wang Jianquan Liang Zhizhao Chen Herbert Meier |
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Affiliation: | 1. School of Chemistry and Chemical Engineering, State Key Lab of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510641, China 2. Institute of Organic Chemistry, Johannes Gutenberg-Universit?t Mainz, Duesbergweg 10-14, 55099, Mainz, Germany
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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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