Anion Transporters Based on Noncovalent Balance including Anion−π, Hydrogen, and Halogen Bonding HuangWen-Long WangXu-Dong LiSen ZhangRui AoYu-Fei TangJun WangQi-Qiang WangDe-Xian 2019 Anion transmembrane transport mediated by novel noncovalent interactions is of central interest in supramolecular chemistry. In this work, a series of oxacalix[2]­arene[2]­triazine-derived transporters <b>1</b> and <b>2</b> bearing anion−π-, hydrogen-, and halogen-bonding sites in rational proximity were designed and synthesized by a one-pot strategy starting from gallic acid ester derivatives and mono- or di-halogen-substituted triazines. <sup>1</sup>H NMR titrations demonstrated efficient binding of <b>1</b> and <b>2</b> toward Cl<sup>–</sup> and Br<sup>–</sup> in solution, giving association constants in the range of 10<sup>2</sup>–10<sup>4</sup> M<sup>–1</sup>. Cooperation of anion−π, hydrogen, and halogen bonding was revealed as a driving force for anion binding by single-crystal structures of two complexes and density functional theory calculations. Fluorescence assays indicated that compounds <b>1</b> are efficient chloride transporters with effective concentrations (EC<sub>50</sub>) falling in the range of 3.1–7.4 μM and following an order of <b>1a</b> > <b>1b</b> > <b>1c</b> > <b>1d</b>. The contribution of halogen bonding and cooperative noncovalent bonds to ion transport was then discussed. Significantly, transporters <b>1</b> exhibit high anticancer activity. In the presence of <b>1</b> and KCl (60 mM), the cell survival of HCT116 reduces to 11.9–24.9% with IC<sub>50</sub> values in the range of 52.3–66.4 μM.