Functionalized aromatic-bis(benzothiazoles) have been synthesized by our group and have shown promise as conductive n-dopable polymers and oligomers. When reduced (n-doped) these materials typically exhibit conductivity on the order of tens of S/cm. Here we examine the material properties of this family of derivatized, conductive aromatic-bis(benzothiazoles). A variety of synthetic approaches have been examined to produce these polymers and oligomers, and will be discussed. Material characterization has been accomplished by spectro-electrochemistry, nuclear magnetic resonance (NMR), electron spin resonance (ESR), Fourier Transform Infrared (FTIR) spectroscopy, and direct current (DC) conductivity.