11-mercaptoundecanoic-acid and dodecylmercaptan

Biomaterial-associated infections caused by pathogenic bacteria have important implications on human health. This study presents the design and preparation of a smart surface with pH-responsive wettability. The smart surface exhibited synergistic antibacterial function, with high liquid repellency against bacterial adhesion and highly effective bactericidal activity. The wettability of the surface can switch reversibly between superhydrophobicity and hydrophobicity in response to pH; this controls bacterial adhesion and release. Besides, the deposited silver nanoparticles of the surface were also responsible for bacterial inhibition. Benefiting from the excellent liquid repellency, the surface could highly resist bacterial adhesion after immersing in a bacterial suspension for 10 s (85%) and 1 h (71%). Adhered bacteria can be easily eliminated using deposited silver nanoparticles during the subsequent treatment of alkaline bacterial suspension, and the ratio of deactivated bacteria was above 75%. After the pH returned to neutral, the deactivated bacteria can be easily released from the surface. This antibacterial surface showed an improved bacterial removal efficiency of about 99%. The results shed light on future antibacterial applications of the smart surface combining both bactericidal and adhesion-resistant functionalities.

Topics: Anti-Bacterial Agents; Bacterial Adhesion; Copper; Escherichia coli; Fatty Acids; Hydrogen-Ion Concentration; Metal Nanoparticles; Silver; Staphylococcus aureus; Sulfhydryl Compounds; Wettability

We describe a new methodology for the fabrication of controllably displaceable monolayers using a carboxyl-functionalized self-assembled monolayer and in situ Fischer esterification, a simple and reversible chemical reaction. Using an 11-mercaptoundecanoic acid monolayer as a model system, we show that in situ esterification results in the creation of subtle chemical and structural defects. These defects promote molecular exchange reactions with n-dodecanethiol molecules, leading to the complete and rapid displacement of the exposed areas. Displacement results in well-ordered crystalline n-dodecanethiolate monolayer films. We also show that the complementary hydrolysis reaction can be employed to quench the reacted monolayer, significantly hindering further displacement. The generality of reversible lability was tested by applying the in situ esterification reaction to the structurally distinct carboxyl-functionalized molecule 3-mercapto-1-adamantanecarboxylic acid. Beyond its applicability to create mixed-composition monolayers, this methodology could be combined with chemical patterning techniques, such as microdisplacement printing, to fabricate complex functional surfaces.

Topics: Esterification; Fatty Acids; Gold; Models, Molecular; Spectrophotometry, Infrared; Sulfhydryl Compounds