Innovative Synthesis and Functions of Curved π-Conjugated Molecules

Creation of novel π-conjugated molecules is an important topic. In this account, one idea for creation of π-conjugated molecules by using distorted conformation has been demonstrated. Planarization of distorted molecules enabled synthesis of heteroatom-containing porphyrin derivatives. Furthermore, dearomatization reaction proved effective to construct distorted conformations from planar π-conjugated molecules under mild reaction conditions. According to this protocol, we have succeeded in the synthesis of heteroatom-containing curved π-conjugated molecules, which have never been achieved by conventional protocols. In particular, a nitrogen embedded buckybowl is the first example of a buckybowl with a heteroatom in its central position, exhibiting unique properties due to incorporation of heteroatom with a curved π-surface.