Synthesis of Shape-Persistent Macrocycles with Three 1,8-Diazaanthracene Units and Their Packing in the Single Crystal

The synthesis of four shape-persistent macrocycles with three 1,8-diazaanthracene units each is reported (2,3a-3c). For two of them single crystals could be obtained and the structures in the crystal be solved. The structures reveal that macrocycle 2 self-dimerizes in the solid state; surprisingly it also forms a stable dimer in solution. The reason for this is seen in unusually efficient dispersion interactions as a consequence of the large contact areas in the dimer. All macrocycles are assessed as to their applicability in lateral polymerizations in the single crystal as well as in solution.