Both reduced zirconocene ("Cp2Zr") and zero valent lithium are known to induce coupling of alkynes to form dimers, oligmers, and polymers. Established work from Fagan et al., Tilley et al., and Eisch et al. was used as the basis for the synthesis of desired targets. First, the attempted syntheses of novel Group IV metalloles from a zirconocene intermediate were studied. There was no conclusive data to state that 2,3,4,5-tetraphenylzirconacyclopentadiene will undergo metallacycle transfer with CrCl3 and FeCl3. The presence of zirconocene dichloride suggests that metallacycle transfer may have occurred, which warrants further investigation. Monomers, 1-bromo-4-hex-1-ynyl-benzene, 1-bromo-3-(phenylethynyl)benzene, and p-dihex-1-ynylbenzene, were synthesized successfully via Sonogashira coupling. Attempts to synthesize novel monomers via lithium and "Cp2Zr" had mixed results. 1H NMR acquisition of the hydrolyzed product from zirconocene-coupling of 1-bromo-3-(phenylethynyl)benzene appeared to be successful. Lastly, lithium and "Cp2Zr" induced polymerization of novel monomers and known monomers were attempted. Metallacycle transfer from the zirconocene intermediate polymers to thiophene, thiopheneoxide, thiophenedioxide, and phosphole were attempted. However, limited characterization was completed. 1H NMR acquisitions suggest polymer by the loss of resolution and broadening of resonance signals, but further characterization via GPC is required. Monomers, and polymers were characterized using various means such as 1H, 13C, 31P, 119Sn NMR spectroscopy, UV-Vis spectroscopy, AIMS AccuTOF-DART mass spectrometry and GPC.