Synthesis and Qualitative Analysis of BACy and Its Self‐polymer

Many synthetic strategies of a reversible cross‐linker N,N′‐bis(acryloyl)cystamine (BACy) involve the typical condensation between the amino group of cystamine and the acyl group of acryloyl chloride in the mixed‐phase solvent system. In this study, the synthesis of BACy was performed in pure organic phase during the whole process. The yield and purity of synthesized BACy were comparable to those from aqueous/organic phase procedures. In addition, polymerization of BACy was also carried out by free radical reaction to prepare the self‐polymer and hydrogel which were characterized with FT‐IR, DSC and UV/VIS spectrophotometer. Notably, the BACy and its self‐polymer were both cleavable when exposed to the reducing agents, i.e. 1,4‐dithiothreitol (DTT) and 2‐mercaptoethanol (β‐ME). Interestingly, the reduced product of BACy contains vinyl and thiol groups, which could be further applied to the co‐polymerization with other monomeric units. On the other hand, carefully controlled reduction of BACy self‐polymer may be used to create the modified polymers with available thiol‐end groups for further chemistry. Together, our study provides modified procedure for BACy synthesis and characteristics of BACy self‐polymer and hydrogel. Further application of BACy and its self‐polymer in developing polymers with additional functionality is anticipated.