Synthesis of rigid polycyclic secondary diamines: Bis-(2,3:6,7-iminodimethylene)anthracene and bis-(2,3:6,7-iminodimethylene)-9,10-dicarboxyethenoanthracene.

The synthesis of two rigid polycyclic secondary diamines, bis-(2,3:6,7-iminodimethylene)anthraceneand bis-(2,3:6,7-iminodimethylene)-9,10-dicarboxyethenoanthracene,by means of Diels-Alder reaction between 1,2,4,5-tetra(dibromo?methyl)benzeneand maleimides followed by imide reduction, is described. Furthermore,these two cyclic secondary diamines undergo acylation with N-protectedamino acids, thus providing functionalized, amphiphilic, and chiralbuilding blocks for incorporation into supramolecular systems