Disulfide–yne reaction: controlling the reactivity of a surface by light

Abstract

In this paper we provide new insight into the disulfide–yne photo reaction, which is similar but different from the well-known thiol–yne photoclick reaction. We show that, unlike the stable product generated from thiol–yne chemistry, the vinyl dithioether structure obtained from disulfide–yne reaction exhibits unique reactivity with thiols and disulfides, which can be used for surface photochemistry to fabricate reactive and dynamic surfaces. The possible mechanism for the unique reactivity of vinyl dithioether structure was discussed. We demonstrated that disulfide–yne reactions are highly compatible with thiol–yne chemistry, but offer the flexibility and dynamic nature that is lacking in thiol–yne chemistry, thus could be a good replenishment for the existing thiol–yne toolbox.