Synthesis of novel dendritic molecules based on pyrroloanthracene units

Abstract

Novel pyrroloanthracenes were efficiently synthesized starting from Diels-Alder adducts of anthracene. Some of these orthogonally bridged, rigid and bulky compounds were used as building blocks for the construction of monodisperse dendritic macromolecules. Molecular masses over 4 kDa could be obtained. Further propagation was problematic because of the particular stability of the 4-(1-pyrrolyl)benzyl cation causing the instability or difficulty of formation of the analogous benzyl ether linkage in the proposed dendritic structures.