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Tetrakis(benzoxazine) calix[4]resorcinarenes as hosts for small molecules

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Abstract

Tetrakis(l,3-dihydrobenzoxazine) calix[4]resorcinarenes 4–6 were synthesized via the Mannich reaction from the corresponding resorcin[4]arenes 1–3 with S-(−)-α-methylbenzylamine or R-(+)-α-methylbenzylamine and formaldehyde (aq.). The products were well characterized by FT-IR, 1H NMR, 13C NMR spectroscopies and single crystal X-ray diffraction analysis. Molecular structures of compounds 4, 5 and 6 showed the same R/S configuration to the starting amines. Compounds 4–6 are stabilized by a collar of intramolecular hydrogen bonding networks between the hydroxy groups and the oxygens from the benzoxazine rings. Compounds 4 and 5 could encapsulate the guest molecules of acetone and dichloromethane, respectively. The UV and 1H NMR titration experiments were performed to study the host-guest chemistry between compound 4 and small acetone molecules, indicating that compound 4 exhibited encapsulation behavior towards acetone molecules through hydrogen bonding interactions.

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Acknowledgements

This project was supported by National Natural Science Foundation of China (90922008).

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Authors and Affiliations

  1. Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’anshan, 243002, Anhui, People’s Republic of China

    Xin-Min Zhou, Qing Wang, Meng Sun, Jing-Long Liu, Ai-Quan Jia & Qian-Feng Zhang

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  1. Xin-Min Zhou
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Contributions

XZ wrote the main manuscript text, QW, MS prepared Figs. 3, 4, 5, 6, 7, 8 and 9, JL prepared Figs. 1 and 2, AJ prepared Figs. 10 and 11, QZ revised the manuscript. All authors reviewed the manuscript.

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Correspondence to Qian-Feng Zhang.

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Zhou, XM., Wang, Q., Sun, M. et al. Tetrakis(benzoxazine) calix[4]resorcinarenes as hosts for small molecules. J Incl Phenom Macrocycl Chem 103, 289–299 (2023). https://doi.org/10.1007/s10847-023-01195-0

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  • DOI: https://doi.org/10.1007/s10847-023-01195-0

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