The synthesis ora new bisfuranyl monomer, 2,7-bis(2-furanyl)-1,6-methano[10]annulene, is presented. Its properties and those of its polymer, synthesized via electropolymerization, are compared to those of the known furan-arene-furan monomers and their respective polymers. Investigation using UV-vis spectroscopy, cyclic voltammetry, and spectroelectrochemistry indicated that the 1,6-methano[101 annulene copolymer has properties rivaling those of the copolymers containing traditional aromatic cores. These results are rationalized in conjunction with DFT calculations, and they further the premise that 1,6-methano[10]annulene can be viewed as a viable building block for advanced pi-conjugated electronic materials.