Disulfide metathesis sulfur iodine interaction and photoswitchability

The idea of constitutional dynamic chemistry (CDC) and dynamic combinatorial chemistry (DCC) is widespread in the literature using the chemistry of disulfides. The synthesis of unsymmetrical diaryl disulfides is challenging due to the presence of a weak S-S bond. We report herein the synthesis of unsymmetrical diaryl disulfides from two symmetrical disulfides via a cross-metathesis reaction which was controlled by a weak sulfur iodine (S I) interaction. The unsymmetrical disulfides were stable in acetonitrile solution in the presence of N -iodosuccinimide (NIS), and found to be reversibly photoswitchable to the symmetrical disulfides under visible light irradiation. N -iodosuccinimide (NIS) promoted and sulfur iodine (S I) interaction controlled cross-metathesis reaction of symmetrical to unsymmetrical disulfides is reported. The photoswitchability is shown of an unsymmetrical to symmetrical diaryldisulfide.