Construction of Topological Supramolecules Utilizing Complementary Salt Bridge Formation and Their Application

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A hetero-stranded double helix with a controlled helix sense was designed and synthesized from an optically active dimeric amidine and its complementary achiral dicarboxylic acid strand with conjugated m-diethynylbenzene backbones, being stabilized by the salt bridges. The dimerization of carboxylic acid derivatives bearing an amino or a formyl group at one end was significantly enhanced in benzene in the presence of an optically active amidine dimer to afford a complementary double helix stabilized with salt bridges. An optically active [2]catenane was synthesized by utilizing amidinium-carboxylate salt bridge. The relative motion of the two macrocyclic components was completely controlled by an acid/base or Zn^<2+>/cryptand control.