Poly-3,4-dihydroxybenzylidenhydrazine, a different analogue of polydopamine

Abstract

In this article, 3,4-dihydroybenzylidenehydrazine is synthesized for the first time, and its properties as a dopamine analogue for polymerization are investigated. Using an oxidative polymerization reaction, the reaction mechanism as well as the coating ability of the new polymer is determined and compared to that of polydopamine. The polymerization reactions were performed in a mixture of methanol–water with NaIO4 as an oxidation reagent. The polymer was used as a coating on both glass surfaces with a thickness of ∼5 nm as determined by AFM, as well as on TiO2 nanoparticles. For the latter, SEM/TEM and the pH-dependent variation of zeta potential were measured. As a free polymer, poly-3,4-dihydroxybenzylidenhydrazine was investigated by UV-Vis, ss-NMR, and FTIR, and a variety of monomeric units were found in the polymer matrix. The solubility in methanol or DMSO of the monomer and the slight solubility of the polymer allowed us to study the fluorescence and cyclic voltammetry properties for both the monomer and polymer.

Keywords

• polydopamine analogues
• fluorescence
• surface coating
• structural analysis
• cyclic voltammetry