Synthesis and characterization of alpha,alpha'-bis (aminomethyl)oligothiophenes and their related compounds

We have synthesized and characterized a series of novel compounds of alpha, alpha'-bis(aminomethyl)oligothiophenes and their related compounds whose degree of polymerization spans two (dimer) to five (pentamer). The compounds presented in our studies are alpha,alpha'-bis [(2,2,5,5-tetramethyl-1-aza-2,w5-disilacyclopenthyl)methyl]oligothiophene, alpha,alpha'-bis(aminomethyl)oligothiophene dihydrochloride and alpha,alpha'-bis(aminomethyl)oligothiophene. These compounds exhibit desired chemical activity while maintaining controllable electronic properties. The synthetic processes of the oligothiophenes are as follows: 2-aminomethylthiophene is first 'protected' and the thiophene rings are coupled using standard Grignard methods. The protected groups are removed at the final stage of the reaction. The compounds show unique properties; for example alpha,alpha'-bis(aminomethyl)oligothiophene dihydro chloride is soluble in water. The results of electronic spectra and titration are also presented.