A new Schiff base, 4-((6-ethoxybenzothiazole-2-ylimino)methyl)benzene-1,2-diol (3,4-HBAEBT) was synthesized by the condensation reaction of 3,4-dihydroxybenzaldehyde (3,4-HBA) and 2-amino-6-ethoxybenzothiazole. The Schiff base, then, was converted to its polymer derivatives by oxidative polycondensation reaction in both organic (P-1) and aqueous alkaline medium (P-2). Spectral observations indicated different structural properties for each polymerization condition. Organic and aqueous alkaline medium produced poly(ether) and poly(phenol) structures, respectively. The obtained polymers were separately studied with respect to optical, electrochemical, electrical and thermal properties. With exception of thermal degradation behaviors, the other investigated properties as well as morphological characteristics of both polymers were considerably different. In the fluorescence measurements a solvatochromic effect was recorded and the emission colors of the polymers could be changed as turquoise-green by solvent change.