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Interconversion of host–guest components in supramolecular assemblies of polycarboxylic acids and reduced Schiff bases

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Abstract

Eight supramolecular assemblies of benzene-1,3,5-tricarboxylic acid (H3BTC) and benzene-1,2,4,5-tetracarboxylic acid (H4BTtC) with reduced Schiff base of flexible backbone having phenolic and pyridyl groups, i.e., 1,2-bis(2-hydroxybenzylamino)ethane, 1,3-bis(2-hydroxybenzylamino)propane, 1,4-bis(2-hydroxybenzylamino)butane and 1,4-bis(4-pyridinylmethylamino)butane have been constructed by proton transfer reaction. H3BTC forms host–guest type assemblies with amines having phenolic functionality, while a layered structure was obtained with pyridyl functionalized amine. H4BTtC also formed host–guest assemblies with the diamines where reduced Schiff base acts as host and acid moiety acts as the guest. Different conformations of the diamines were observed in these assemblies. Theoretical studies were performed to analyze the effect of varied chain lengths of diamines on hydrogen bond interaction energy of the adducts.

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Acknowledgments

The authors gratefully acknowledge CSIR, New Delhi, India, for financial assistance.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247 667, India

    Udai P. Singh, Kapil Tomar & Sujata Kashyap

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  1. Udai P. Singh
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  2. Kapil Tomar
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  3. Sujata Kashyap
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Correspondence to Udai P. Singh.

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Singh, U.P., Tomar, K. & Kashyap, S. Interconversion of host–guest components in supramolecular assemblies of polycarboxylic acids and reduced Schiff bases. Struct Chem 27, 1027–1040 (2016). https://doi.org/10.1007/s11224-015-0699-0

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