Molecular Recognition Properties of Biphen[4]arene |
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| Authors: | Suxiang Ma Huanqing Chen Prof?Dr Jian Li Prof?Dr Xueshun Jia Prof?Dr Chunju Li |
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| Affiliation: | 1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, P.R. China;2. Department of Chemistry, Center for Supramolecular Chemistry and Catalysis, Shanghai University, Shanghai, P.R. China;3. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, P.R. China |
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| Abstract: | Biphenn]arenes (n=3, 4) are a new family of macrocyclic hosts. Here, we describe the molecular recognition behavior of hydroxylated biphen4]arene (OHBP4) for the first time. A series of cationic guests with different sizes and shapes, including quaternary ammonium salts ( 1? PF6 and 2? PF6), pyridinium‐based guests ( 3? 2 PF6– 6? 2 PF6), and cobaltocenium hexafluorophosphate ( 7? PF6), were chosen as model guest molecules. OHBP4 exhibits good selectivity towards the 2,7‐dibutyldiazapyrenium bis(hexafluorophosphate) ( 4? 2 PF6) axle to form a 2]pseudorotaxane‐type complex. In contrast, hydroxylated biphen3]arene (OHBP3) cannot bind with this big guest. In addition, OHBP4 strongly interacts with adamantane derivative 2? PF6 and cobaltocenium 7? PF6, which have tridimensional shape and relatively large size. The association constant of the 7 +?OHBP4 complex in 1:1 (v/v) D6]acetone/CD2Cl2 solution is up to 3100±300 m ?1. |
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| Keywords: | biphen[n]arenes macrocyclic hosts molecular recognition supramolecular chemistry |
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