The cyclopolymerization of 1,8-diethynylnaphthalene(DEN) and its copolymerization with diethyl dipropargylmalonate(DEDPM) were carried out by various transition metal catalysts. MoCl5-based catalyst was found to be very effective and gave almost a quantitative polymer yield. The resulting dark-brown homopolymer(PDEN) was partially soluble in chloroform, tetrahydrofuran, and dimethyl sulfoxide, whereas copolymer (1:1) with number average molecular weight (MnBAR) of 2.1x10(4) by GPC showed good solubility in those solvents. The structure of the polymers was analysed by IR, NMR, and UV-VIS spectroscopies. From the spectral and solubility data, it is proposed that cyclized products with the conjugated system are formed. Room temperature conductivities of the I2-doped homo and copolymer were found to be about 7.5x10(-3) and 5.1x10(-3) S/cm, respectively.