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Three pillar5arene dimers, bridged by a flexible aliphatic chain (H1) or a relatively rigid phenylene unit (H2 and H3), were synthesized, with the possible synthetic strategies being discussed. The dimers could significantly enhance the binding affinities toward neutral model substrates in comparison with monomeric 1,4-dimethoxypillar5arene (H4) through the cooperative binding of two pillar5arene moieties. The molecular binding ability and selectivity are discussed from the viewpoints of the size/shape-fit concept and multiple recognition mechanism.
Li et al. (Mon,) studied this question.