Conjugated nanohoops are excellent candidates to study structure-property relationships, as optoelectronic materials and as hosts for supramolecular chemistry. While carbon nanohoops containing aromatics are well studied, antiaromatic units had not been incorporated until recently by our group using dibenzo[a,e]pentalene (DBP). The non-alternant electronic character of the DBP units significantly influences the optoelectronic properties of such nanohoops. We herein summarize our synthetic strategies to DBP-containing nanohoops, 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.