Cyclopolymerization of dipropargyl ether was carried out in nitrogen atmosphere with different initiators (KSCN/KCl/KBr/KI) in dimethyl formamide. The rate of polymerization was determined for different conditions and used for comparing the efficiency of the initiators. KSCN and KI were found to be effective initiators for cyclopolymerization. The resulting polymer exhibits good solubility in common organic solvents and exhibited solvatochromic behaviour. The results from H-1 NMR, FT-IR and UV-Visible spectra of poly(dipropargyl ether), PDPE supported the idea that the resulting polymer possesses polyene structure having cyclic recurring units in the polymer backbone. Conductivity, thermogravimetric analysis and electroactivity of the polymer were also studied. The results from UV-Visible, FTIR spectroscopy and conductivity measurements clearly revealed the doped nature of PDPE.