Cross-Linked Carboxybetaine SAMs Enable Nanoparticles with Remarkable Stability in Complex Media

A photo-cross-linkable carboxybetaine (CB)-terminated thiol with only one CB headgroup was introduced to modify gold nanoparticles (GNPs) via self-assembled monolayers (SAMs). This CB-terminated thiol consists of three moieties: (a) an anchoring thiol group, which binds directly to the GNP surface, (b) a CB terminal group, which is highly resistant to protein adsorption, and (c) a diacetylene group in the middle, which is converted to a poly(enyne) structure during UV irradiation via 1,4-topochemical polymerization. Results show that, after cross-linking, CB-modified GNPs are highly resistant to protein adsorption from undiluted human blood serum and cell uptake, and are stable at low pH and high temperature. This cross-linkable CB thiol holds tremendous potentials for biomedical applications where stable and thin coatings are needed.