Dynamic covalent bonding has had a large impact on the fields of materials science and supramolecular chemistry, ranging from self-healing materials to dynamic combinatorial libraries. We have recently shown that four such reactions are entirely orthogonal, meaning that they are be combined in the same solution with no cross-reactivity between the electrophilic and nucleophilic partners: boronic acids with diols, hydrazide with aldehydes, thiols with conjugate acceptors, and metal chelations. An NMR spectra modeling program was used to conclusively demonstrate this orthogonality. We refer to the dynamic pairs as TORC units, Tunable Orthogonal Reversible Covalent bonds. As an extension, complex peptides containing the pairs create predictable quaternary structures - from loops, to figure eights and ladders, to Vernier oligomers. Further, with a specific conjugate acceptor derived from Meldrum’s acid, amines and thiols can be “clicked” and chemically trigger to “declick”, returning the amines and thiols undisturbed. All these strategies can be used to create dynamic polymers, whose structures are tuned by the choice of the TORC pairs, and in some cases and be degraded back to starting materials. Applications in polymer chemistry and supramolecular chemistry will be presented.

Dynamic covalent bonding: Complex quaternary structures and clicking/declicking applications

254th National Meeting (2017)

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