2,7-Dibromoazadibenzocyclooctyne (DIBAC-Br-2) was prepared as a pro-monomer unit that could be modified by the metal-free strain-promoted azide-alkyne cycloaddition (SPAAC). Click cyclization of DIBAC-Br-2 with five different benzyl azides produced a homologous series of monomers with different functionality on the resulting triazole ring, ranging from electron-withdrawing to electron-donating substituents. Using this series of monomers, in combination with 2,7-dialkylfluorene as a comonomer, five different conjugated polymers were prepared via Suzuki polycondensation, each having different electronic properties. The resulting copolymers exhibited M-w values ranging from 5 to 10 kDa and PDI values in the 1.5-2 range. These polymers were characterized by H-1 NMR spectroscopy, optical spectroscopy, and cyclic voltammetry. Finally, a coumarin-containing oligomer was synthesized and used to demonstrate a photo-cross-linking scheme via [2 + 2] cycloaddition.