Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors

Ju Hyun Oh; Jeong Hyeon Kim; Dong Sub Kim; Hye Jin Han; Vincent M Lynch; Jonathan L Sessler; Sung Kuk Kim

doi:10.1021/acs.orglett.9b01515

Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors

Org Lett. 2019 Jun 7;21(11):4336-4339. doi: 10.1021/acs.orglett.9b01515. Epub 2019 May 24.

Authors

Ju Hyun Oh¹, Jeong Hyeon Kim¹, Dong Sub Kim², Hye Jin Han¹, Vincent M Lynch², Jonathan L Sessler², Sung Kuk Kim¹

Affiliations

¹ Department of Chemistry and Research Institute of Natural Science , Gyeongsang National University , Jinju 660-701 , Korea.
² Department of Chemistry , The University of Texas at Austin , 105 East 24th Street, Stop A5300 , Austin , Texas 78712-1224 , United States.

PMID: 31125242
DOI: 10.1021/acs.orglett.9b01515

Abstract

A molecular cage, macrobicycle 2, containing amide and pyrrole groups as hydrogen-bonding donors and imine groups as hydrogen-bonding acceptors has been synthesized. Compound 2 was found to recognize tetrahedral oxyanions with high affinities, such as H₂PO₄^-, HSO₄^-, SO₄^2-, and HP₂O₇^3-, as well as the spherical halide anions, in chloroform. A single-crystal X-ray diffraction analysis revealed that compound 2 formed a 1:1 complex with H₂PO₄^- in the solid state.