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Polycyclic conjugated hydrocarbons (PCHs) containing antiaromatic rings are of fundamental and technical interest. [N]naphthylene is an intriguing family of PCHs consisting of alternatingly fused naphthalenoids and antiaromatic cyclobutadienoids (CBDs). We recently reported the first three regioisomers of the [N]naphthylene family, synthesized by catalytic arene-norbornene annulation (CANAL) reaction followed by acidic aromatization. We now report an iterative strategy for CANAL synthesis allowing us to synthesize the forth regioisomer, edge-bent [3]naphthylene. The optoelectronic properties, local paratropicity, and crystal packing of the edge-bent [3]naphthylene were studied and compared with its closely related regioisomer, center-bent [3]naphthylene.