Surface Modification of Pseudoboehmite-Coated Aluminum Plates with Squaramic Acid Amphiphiles

[Image: see text] The functionalization of interfaces has become very important for the protection or modification of metal (metal oxides) surfaces. The functionalization of aluminum is particularly interesting because of its relevance in fabricating components for electronic devices. In this work, the utilization of squaramic acids for the functionalization of aluminum substrates is reported for the first time. The physicochemical properties of the interfaces rendered by n-alkyl squaramic acids on aluminum metal substrates coated with pseudoboehmite [Al(O)x(OH)y] layers are characterized by contact angle, grazing-angle Fourier-transform infrared spectroscopy, atomic force microscopy, scanning electron microscopy, X-ray photoelectron spectroscopy, and matrix-assisted laser desorption ionization time-of-flight. Moreover, we could confirm the squaramic functionalization of the substrates by diffuse reflectance UV–vis spectroscopy, which cannot be used for the characterization of UV–vis-inactive substrates such as carboxylates and phosphonates, commonly used for coating metallic surfaces. Remarkably, the results of sorption experiments indicate that long-chain alkyl squaramic acid desorbs from activated-aluminum substrates at a reduced rate compared to palmitic acid, a carboxylic acid frequently used for the functionalization of metal oxide surfaces. Theoretical calculations indicate that the improved anchoring properties of squaramic acids over carboxylates are probably due to the formation of additional hydrogen bonding interactions on the interface. Accordingly, we propose N-alkyl squaramic acids as new moieties for efficient functionalization of metal oxides.