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Synthesis, structure, and anion binding of functional oxacalix[4]arenes

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Abstract

Oxacalix[4]arenes obtained from the highly efficient, one-pot SNAr reaction were post-macrocyclization functionalized through the reduction of nitro groups and hydrolysis of the ester groups to obtain several derivatives of desired solubility. The difficulties in basic hydrolysis of ester groups were overcome via developing an acid hydrolysis method for tert-butyl ester derivatives of this class. The synthesis of symmetrical oxacalix[4]arenes from an unsymmetrically substituted precursor was also explored via a multiple step fragment coupling approach. Compounds 17 & 18 adopted 1,3-alternate conformations in the solid state as most oxacalix[4]arenes did, and a chair (zigzag) conformation was revealed for tetraamido oxacalix[4]arene (6a) by X-ray single crystal analysis. The tetraureido oxacalixarene (7) showed strong association towards various anions such as F, Cl, Br, I, Ac, and HSO4 with a 1 : 1 stoichiometry as revealed by 1H NMR analysis and UV-vis measurements.

Graphical abstract: Synthesis, structure, and anion binding of functional oxacalix[4]arenes

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Publication details

The article was received on 15 Mar 2019, accepted on 30 Apr 2019 and first published on 30 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00613C
Org. Biomol. Chem., 2019, Advance Article

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    Synthesis, structure, and anion binding of functional oxacalix[4]arenes

    J. Ma, X. Fang, M. Xue and Y. Yang, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00613C

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