As fascinating examples of closely connected multiple π-electronic systems involving noncovalent interactions, the cooperatively interlocked [2+1]-type anion complexes of well-designed π-electronic molecules are reported. The anion-responsive π-electronic molecules investigated in this study are the boron complexes of dipyrrolyldiketones bearing arylethynyl moieties at the pyrrole α-positions. Diverse substituents were introduced at the terminal aryl moieties, thus controlling the cooperativity to form [2+1]-type complexes. Theoretical studies showed that this cooperativity was induced by effective interactions between the introduced arylethynyl moieties. The investigations of the anion-binding processes showed that the first and second bindings to the guest anion were energetically almost equivalent, indicating the fundamental and important features of the electronic states of the halide anions. Furthermore, the interlocked anion complexes, whose geometries were distorted from the orthogonal arrangements, had the racemic states of the chiral conformations, either of which was induced by ion pairing with an appropriate chiral π-electronic cation, resulting in the chiroptical property as shown by circular dichroism.