Natural channel proteins are complex in structure and marvelous in function. Chemists have constructed a variety of simple synthetic structures with the goal of mimicking the function of channel proteins. The objective of this review is to recall the development of synthetic ion channels with controllable transport behaviour over the past three decades. The most inspiring channels with voltage-, ligand-, light- and mechano-gating, as well as rectifying behaviours have been discussed in regard to their structures and functions in the hope of providing an easily accessible understanding of the field to the general reader. In addition, promising directions and major remaining challenges are also addressed.