Synthesis of heteroatom-containing curved π-conjugated molecules

Abstract

Recently, π-conjugated molecules with curved-π surface have attracted considerable interest for their unique properties originating from their curved structures. However, most of them consist of only carbon and hydrogen atoms. In these situations, we have developed novel synthetic protocols for construction of distorted structures directly from 2D π-conjugated molecules under mild reaction conditions. By applying phenol and aniline oxidation methods, we have succeeded in the synthesis of highly distorted cyclophanes, π-extended heterohelicenes, and highly twisted porphyrin oligomers. Furthermore, we have succeeded in the synthesis of a nitrogen-embedded buckybowl as a novel bowl - shaped π-conjugated molecule with a pyrrolic nitrogen in its skeleton. These heteroatom containing curved-n conjugated molecules exhibit unique characteristics due to the combination of the curved structure with heteroatoms such as circularly polarized luminescence, strong C60 binding, and near IR electrochromism. We believe that the chemistry of heteroatom containing curved-π conjugated molecules would enhance the potential of three -dimensional π -conjugated molecules for molecular materials.