The dynamic covalent reaction based on diselenide-containing crown ether irradiated by visible light

Photochemical Transformations of Peptides Containing the N-(2-Selenoethyl)glycine Moiety

“…Similarly, Qi et al reported on the metathesis reaction between the low-molecular-weight compound, BnSe 2 , and the diselenide-containing crown ether, BC7Se 2 , under visible light, which was found to be weaker than the reaction between noncyclic compounds due to the cyclic topology of BC7Se 2 . 15 In order to determine whether there are any interactions in the studied systems, we performed noncovalent interaction (NCI) calculations. Accordingly, four products, including CM2A, CM2B, CM2C, and C2T, formed by the reaction between Cyclo(Se−Se)2 and BBSe 2 were taken into consideration to study the possible interactions.…”

“…Therefore, we hypothesized that noncovalent interactions could play an important role in maintaining the cyclic form of the peptides and thus reduce the ability of the peptides to undergo diselenide metathesis. Similarly, Qi et al reported on the metathesis reaction between the low-molecular-weight compound, BnSe 2 , and the diselenide-containing crown ether, BC7Se 2 , under visible light, which was found to be weaker than the reaction between noncyclic compounds due to the cyclic topology of BC7Se 2 …”

“…Similarly, Qi et al reported on the metathesis reaction between the low-molecular-weight compound, BnSe 2 , and the diselenide-containing crown ether, BC7Se 2 , under visible light, which was found to be weaker than the reaction between noncyclic compounds due to the cyclic topology of BC7Se 2 . 15 …”

“…Various dynamic covalent bonds (DCBs), including boronate ester linkages, imine linkages, and disulfide linkages, have been widely used for biomedical applications such as wound dressing, antibacterial activity, and gene delivery . In recent years, diselenide bonds have emerged as a new class of DCBs capable of undergoing metathesis in response to many stimuli, including pH, heat, and light. − In addition, osmotic pressure has been shown to be an external force to induce the diselenide exchange reaction that can be modulated by varying the concentration of NaCl . More recently, pulse sonication has been demonstrated to cleave the Se–Se bond in polymers more rapidly, but not as effectively for small molecules, thus providing a more selective method to induce diselenide metathesis .…”