A study of the oxidation and polymerisation of meta substituted phenol and aniline derivatives

The objective of this paper is the study of the electrochemical oxidation and subsequent polymerisation of 1,3-dihydroxybenzene, 3-aminophenol and 1,3-phenylenediamine at pH 7. These related monomers were subsequently utilised by the authors in the production of pinhole free masks for the construction of features on gold surfaces of nanometer dimensions (neutral pH was required due to the use of biological templates). It is shown that whilst the electrochemical oxidation of 1,3-phenylenediamine is very similar to that of 3-aminophenol, it is quite dissimilar to that of 1,3-dihydroxybenzene and this can be attributed to the lack of interaction between the substituents on the ring due to their meta orientation. This behaviour can be correlated with differences in the HOMO values of the molecules as calculated using Crystal98. X-ray photoelectron spectroscopy was used to characterise the polymer films and their thin layer nature.