Conjugated Nanohoops with Dibenzo[a,e]pentalenes as Nonalternant and Antiaromatic π-Systems

Conjugated nanohoops are excellent as candidates for studying structure–property relationships, as optoelectronic materials, and as hosts for supramolecular chemistry. Whereas carbon nanohoops containing aromatics have been well studied, antiaromatic units had not been incorporated until our group recently did so, using dibenzo[a,e]pentalene (DBP). The nonalternant electronic character of the DBP units significantly influences the optoelectronic properties of such nanohoops. Here, we summarize our synthetic strategies toward DBP-containing nanohoops, together with their structural and electronic properties, chirality, and host–guest chemistry. We demonstrate how incorporating antiaromatic units leads to unique properties and opens new synthetic avenues, making such nanohoops attractive as potential electronic materials.1 Introduction2 Synthesis3 Structural Properties4 Electronic Properties5 Chirality6 Host–Guest Chemistry