Using living ROMP with G-2nd generation, we synthesized and reported of novel Homopolymers (P1–P4) and a random copolymer (P5). Essential monomers, carbazolovinylene (M1) and phenothiazinovinylene (M2), containing octyl chains, were prepared via McMurry dimerization. M1 polymerized under variety of circumstances, whereas M2 necessitated more stringent environmental controls due to its lower ring strain. GPC analysis revealed Mn values of 8.78-20.46 kDa and Mw between 9.38 and 20.46 kDa, indicating controlled polymerization PDIs of 1.06–1.25. UV-Vis spectra indicated λmax values of 327.6–417.5 nm in DCM, with optical band gaps (Egop) between 2.52 and 2.90 eV. Using DFT and TD-DFT methodologies investigated that P4 is absolute soft according to (σ= 3.546 eV), while P5 is treated as hard compounds (σ= 0.639 eV) and These findings demonstrate the effective synthesis of well-defined polymers, providing the groundwork for future research in advanced material applications.