Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Antiparallel Dynamic Covalent Chemistries

Antiparallel Dynamic Covalent Chemistries
Charalampos G. Pappas, Bin Liu, Dávid Komáromy, Sijbren Otto, Bartosz M. Matysiak, Piotr Nowak, Ivica Cvrtila
The ability to design reaction networks with high, but addressable complexity is a necessary prerequisite to make advanced functional chemical systems. Dynamic combinatorial chemistry has proven to be a useful tool in achieving complexity, however with some limitations in controlling it. Herein we introduce the concept of antiparallel chemistries, in which the same functional group can be channeled into one of two reversible chemistries depending on a controllable parameter. Such systems allow both for achieving complexity, by combinatorial chemistry, and addressing it, by switching from one chemistry to another by controlling an external parameter. In our design the two antiparallel chemistries are thiol–disulfide exchange and thio-Michael addition, sharing the thiol as the common building block. By means of oxidation and reduction the system can be reversibly switched from predominantly thio-Michael chemistry to predominantly disulfide chemistry, as well as to any intermediate state. Both chemistries operate in water, at room temperature, and at mildly basic pH, which makes them a suitable platform for further development of systems chemistry.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b02575

DOI: 10.1021/jacs.7b02575

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