Graphene nanoribbons (GNRs), nanometer-wide strips of graphene, are attracting significant attention in materials science as candidates for next-generation carbon materials. As their physical properties mainly depend on their structures, the precise synthesis of structurally well-defined GNRs is highly desirable to control their properties. Herein, we report a step-growth annulative pi-extension polymerization that allows for the rapid and modular synthesis of cove-type GNRs with pyrene and/or coronene diimide repeating units. The structures and photophysical properties of the separated GNRs were confirmed by various spectroscopic analyses. In addition, gas-blow-assisted uniform on-surface self-assembly of the GNRs was accomplished.