Naphthylisoquinoline-appended dipyrrolyldiketone PtII complexes as helical π-electronic systems were synthesized. The PtII complexes, showing chiroptical properties in solution, exhibited anion-binding behaviour, resulting in the formation of anion complexes as pseudo π-electronic anions. In combination with π-electronic cation, the receptor–anion complexes formed charge-by-charge ion-pairing assemblies, with the narcissistic self-sorting columnar structures comprising either of the enantiomers, in the crystal state.

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