Radical-cation salts of sulfur-substituted aromatic compounds, formed upon chemical and electrochemical oxidation of the neutral parent compounds, represent an important class of stable electron-conducting materials with many potential uses in molecular-electronics. Many electronic devices require, however, macromolecular materials bound to an electrode surface. While a large number of sulfur-substituted aromatic compounds capable of forming electron-conducting radical-cations salts have been thus far reported, none of them bears functional groups that could be used to bind these compounds to a polymer backbone or an electrode surface. In this paper, we report the synthesis of functionalized analogs of 1,3,6,8-tetrakis(methylsulfanyl)pyrene, where one of the methylsulfanyl groups has been replaced by an amide group. Substitution of the methylsulfanyl group by the amide group does not inhibit the formation of highly electron-conducting radical-cation salts. N-(3,6,8-Tris(methylsulfanyl)pyren-1-yl)acetamide (3a) forms, upon oxidation with iodine, a radical-cation salt (4a) similar to those formed by the parent 1,3,6,8-tetrakis(methylsulfanyl)pyrene 2. The electron-conductivity of radical-cation salt 4a was found to be 1 S cm(-1) at room temperature. The amide group was also used as a handle to introduce additional functionality on the molecule. Coupling of 3,6,8-tris(methylsulfanyl)pyren-1-ylamine (10) with the gamma-carboxyl group of N-(tert-butoxycarbonyl)-L-glutamic acid alpha-tert-butyl ester was achieved via the formation of a mixed anhydride with isobutylchloroformate. This functionalized 3,6,8-(trismethylsulfanyl)pyrene derivative will be used in polymerization reactions onto electrode surfaces, providing a new surface-bound electroactive polymer with potential applications in molecular devices.