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Issue 7, 2016
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The third orthogonal dynamic covalent bond

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Abstract

Orthogonal dynamic covalent bonds are of interest for the construction of functional systems. The orthogonality of disulfide and hydrazone exchange under basic and acidic conditions, respectively, is well established. However, the integration of boronate esters as the third bond has failed so far because they exchanged too easily, especially under hydrazone exchange conditions. In this report, a collection of bioinspired catechols derived from adhesive natural products from cyanobacteria is screened with phenylboronic acids with proximal alcohols (benzoboroxoles), amines and fluorines to identify the least labile boronate esters. Moreover, Kool's 2-aminophenol catalysts are introduced to selectively accelerate hydrazone exchange without disturbing sufficiently inert boronate esters. Based on these results, we identified three different conditions to selectively exchange disulfides, hydrazones and boronate esters, that is to demonstrate the existence of three orthogonal dynamic covalent bonds. Moreover, their compatibility with functional systems is confirmed by successful hydrazone exchange in multicomponent surface architectures in the presence of intact boronate esters and disulfides.

Graphical abstract: The third orthogonal dynamic covalent bond

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Publication details

The article was received on 11 Mar 2016, accepted on 09 Apr 2016 and first published on 20 Apr 2016


Article type: Edge Article
DOI: 10.1039/C6SC01133K
Citation: Chem. Sci., 2016,7, 4720-4724
  • Open access: Creative Commons BY license
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    The third orthogonal dynamic covalent bond

    S. Lascano, K. Zhang, R. Wehlauch, K. Gademann, N. Sakai and S. Matile, Chem. Sci., 2016, 7, 4720
    DOI: 10.1039/C6SC01133K

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