Synthesis and inclusion phenomena of nitrogen-bridged macrocyclic host molecules 1-4 and related macrocyclic compounds 5-7 are summarized. The new class of macrocycles 1-4 were designed and synthesized by one-step coupling reactions. Cubic cyclophane 5 was also obtained by this method. Because of the preorganized structure of 3 and 4 with four and six pyridine donors, respectively, they strongly bind proton, alkali metal and ammonium ions. They also act as a Cl
- ion receptor in acidic solution. The compound 6 formed inclusion complexes with guanidium ion, urea and water molecules. Compounds 3 and 4 formed stable Cu+ or Ag+ complexes. The dinuclear complex 2 Ag
+ ⊂4 has a short Ag
+…Ag
+ distance (2.78 Å). The halide anions (Cl
-, Br
-, I
-) removed one Ag
+ from 2 Ag
+⊂4 to give Ag
+ ⊂ 4, but further demetallation did not occur. Both silver complexes are stable to sunlight. The preparations of guest-free hosts were achieved by treating Cu
+ ⊂3 or 2 Ag
+ ⊂ 4 with CN
-. Inclusion of neutral guests (NH
3, BH
3) was attempted using these guest-free hosts.
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