Investigation of Antifouling Properties of Surfaces Featuring Zwitterionic α‐Aminophosphonic Acid Moieties

Abstract

Zwitterionic thin films containing α-amino phosphonic acid moieties were successfully introduced on silicon surfaces and their antifouling properties were investigated. Initially, the substrates were modified with a hybrid polymer, composed of poly(methylsilsesquioxane) (PMSSQ) and poly(4-vinyl benzaldehyde) (PStCHO). Next, a Kabachnik-Fields post-polymerization modification (sur-KF-PMR) of the functionalized aldehyde surfaces was conducted with different amines and dialkyl phosphonates. After subsequent deprotection reaction of dialkyl phosphonates, the obtained zwitterionic surfaces were characterized by various techniques and we found excellent antifouling properties of the resulting films.

50th Anniversary Perspective: Polymer Functionalization

“…As bioisosteres of amino acids, α-amino phosphonates and polymers that are functionalized with them are useful for the preparation of biologically active materials for such applications as antifouling, among others . The Kabachnik–Fields reaction offers a mild route to these moieties through the reaction of aldehyde, amine, and phosphonate components (Scheme ).…”

“…As bioisosteres of amino acids, α-amino phosphonates and polymers that are functionalized with them are useful for the preparation of biologically active materials for such applications as antifouling, among others. 179 The Kabachnik−Fields reaction offers a mild route to these moieties through the reaction of aldehyde, amine, and phosphonate components (Scheme 7). Theáto and Tao have pioneered the introduction of the Kabachnik−Fields reaction into polymer science for the preparation of α-amino phosphate functional polymers via a metal-free procedure.…”

Materials Functionalization with Multicomponent Reactions: State of the Art

“…Later, the same group explored the antifouling property of the α-aminophosphonic acids covered silicone surfaces. The results revealed the obvious antifouling ability of zwitterionic polymer covered surfaces against the adhesion of proteins and bacteria …”

“…The results revealed the obvious antifouling ability of zwitterionic polymer covered surfaces against the adhesion of proteins and bacteria. 131 In an interesting study in 2018, Lowe and co-workers described the preliminary procedure for the design and development of the holographic sensor modified with Ugiligands for cocaine detection using a smartphone-based instrument. 132 A library of ligands was designed based on the protein−cocaine interactions, particularly those of human carboxylesterase-1 and catalytic monoclonal antibody GNL7A1.…”

Low-Fouling and Antibacterial Polymer Brushes via Surface-Initiated Polymerization of a Mixed Zwitterionic and Cationic Monomer

“…Contact-active materials are typically coated with positively charged polymers such as polymeric quaternary ammonium compounds with membrane disruptive properties. , They have been shown to have strong antibacterial activity . However, the accumulation of biomaterial by attractive charge interactions of the positively charged surfaces with negatively charged biomolecules or cell fragments causes a loss of function over time and can lead to an immune response and inflammation in vivo. , Antifouling materials, on the other hand, are typically characterized by hydrophilic surfaces. − The latter are often polymeric zwitterions composed of sulfobetaines, phosphobetaines, carboxybetaines, or N -oxides, leading to strong hydration barriers and thus antiadhesive properties for biomolecules and microorganisms. − However, they lack antibacterial properties …”