Synthesis of shape-persistent macrocycles with three 1,8-diazaanthracene units and their packing in the single crystal

摘要

The synthesis of four shape-persistent macrocycles with three 1,8-diazaanthracene units each is reported (2,3 a-3 c). 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. The perfect fit: Two shape-persistent macrocycles such as A form a self-assembled dimer in the single crystal which even under forcing conditions in solution cannot be made to dissociate into the single components.