In this paper, two pillar[5]arene derivatives were prepared that are soluble in water. The structures of the synthesized reactants and water-soluble compounds were illuminated with some characterization techniques such as 1H NMR, 13C NMR, elemental analysis, mass spectroscopy, melting point, and FT-IR. When the thermal stability of these macrocycles was examined by TGA method, it was found that they showed differences depending on the different electronic environments on the main molecular skeleton. The antibacterial activities of two water-soluble pillar[5]arene derivatives against three bacteria (Escherichia coli, Staphylococcus aureus and S. typhimurium) for two concentrations were investigated. Although the antibacterial results are close to each other, the best results were obtained against Staphylococcus aureus bacterium. In addition, the catalytic activities of two water-soluble pillar[5]arene derivatives by reduction of 4-Nitroaniline were investigated. These compounds are a potential choice in the industry because they can be used both as antibacterial material agents and as materials that reduce organic pollutants.