Distinctive concave compounds bearing a nitrogen core and double fused pentagons were synthesized with a palladium-catalyzed intramolecular coupling of 1-chloro-8 H-indolo[3,2,1- de]acridine as the key step. Structural analysis confirmed the formation of bowl-shaped molecules. Experimental characterizations and theoretical calculations reveal the incorporation of nitrogen is crucial to alleviate the pentagon fusing strain, as well as in property regulation.