thiolterminated

Thiolterminated describes a molecule or polymer that contains a sulfhydryl group (-SH) at one terminal end. This functional group provides a reactive handle for bonding to metals, other molecules, or polymers, enabling a wide range of surface and materials applications.

The thiol group is a soft nucleophile with a pKa around 10. In neutral to mildly basic conditions, thiols can form thiolate anions that readily participate in bonding and exchange reactions. On metal surfaces, especially gold, thiols bind through metal–sulfur bonds to form organized structures known as self-assembled monolayers. Thiolterminated ligands are thus commonly used to functionalize gold nanoparticles, electrodes, and sensors. They can also serve as linkers in disulfide exchange and be incorporated into thiol–ene or other click-type chemistries for further modification.

In practice, thiolterminated compounds are prepared by reducing disulfides, by selective introduction of a mercapto group, or by protecting groups that are later removed to reveal the -SH functionality. They are used to cap surfaces or polymers, providing a reactive site for subsequent conjugation with biomolecules, receptors, dyes, or drugs, and to create linkage points for polymer grafting or crosslinking.

Stability and handling considerations include sensitivity to oxidation, which can convert thiols to disulfides, reducing the availability of free -SH groups. Storage under inert atmosphere or rapid use after deprotection is common. The term is widely used across surface chemistry, nanotechnology, and polymer science to denote the presence of a terminal thiol group.