2-Methyl-1,4-naphthoquinones containing 3-[N-(ω-mercaptoalkyl)alkanamide] chains: synthesis, self-assembling, and electrochemical properties

2-Methyl-1,4-naphthoquinone derivatives containing 3-[N-(ω-mercaptoalkyl)alkanamide] chains were synthesized from ω-bromoalkylamine salts of 2-methyl-3-carboxyalkyl-1,4-naphthoquinones in the presence of N,N′-dicyclohexylcarbodiimide at ambient temperature, and then transformed into the corresponding mercapto derivatives. Their self-assembling and electrochemical properties on gold were studied. The influence of an intrachain amide group on the structure and electron transfer properties of self-assembled monolayers were evaluated by comparison with analogous ester and alkyl chain-containing 2-methyl-1,4-naphthoquinones.