Abstract
Here we report the simultaneous formation of doubly and triply dynamic libraries as a result of exchange reactions between functionalized organic building blocks. A combination of three different reversible covalent linkages involving a boronate ester transesterification along with an imine and disulfide exchange was employed to generate a new type of fully organic triply dynamic molecular assembly.
Highlights
M ultidynamic systems capable of constitutional interconversions are of increasing interest, as they efficiently implement chemical diversity and lead to “informed” dynamics with applications in the medical and pharmaceutical industries including drug delivery.[1]
The simultaneous use of several reversible covalent linkages is essential to the expansion of the range of constituents expressed in a Dynamic Combinatorial Library (DCL).[2]
One of the pioneering works on complex orthogonal libraries was presented by Matile, in which the optimized conditions enabling the independent exchange of three orthogonal bonds was presented.[5,11]
Summary
M ultidynamic systems capable of constitutional interconversions are of increasing interest, as they efficiently implement chemical diversity and lead to “informed” dynamics with applications in the medical and pharmaceutical industries including drug delivery.[1]. In other instances, such DCLs have been obtained using different combinations of disulfide, hydrazone, imines, and boronate ester exchange reactions.[8] An interesting achievement was the use two of the abovementioned covalent linkages in the formation of linear smallmolecular motors.[9] Another extraordinary example comes from the Otto group involving an antiparallel dynamic system where two chemistries, thiol−disulfide and thio-Michael exchange, operate simultaneously.[10]
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