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Dynamic covalent bonds: approaches from stable radical species

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Abstract

Reversible covalent bond formation/scission systems, referred to as Dynamic Covalent Chemistry (DCC), have received significant interest in view of the molecular systems, which offer feasible “error-correction” of the targeted chemical structures and the rearrangement of chemical bonds into the proper manner during the synthetic processes. DCC has been widely designed and developed with molecules in chemical equilibria where a set of reactants and a product are both in closed shell molecules. Within a few years, the concept of DCC systems has been extended to the formation of a covalent bond between a set of stable radicals, utilizing a common feature of radical species: the ease of the bond cleavage and formation. Generally, the coupling reactions among radical species are thermodynamically favorable in a down-hill manner with no or extremely small energetic barriers, and the barrier of the dissociation reactions can be minimized by properly designing the radical species. This review highlights the examples of the radicals showing reversible oligomerization–dissociation behavior, which have been or will potentially be utilized as building blocks in DCC, and the recent development of molecular self-assembly based on reversible radical coupling and homolytic cleavage reactions.

Graphical abstract: Dynamic covalent bonds: approaches from stable radical species

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Publication details

The article was received on 29 Jul 2019, accepted on 06 Sep 2019 and first published on 09 Sep 2019


Article type: Review Article
DOI: 10.1039/C9QM00488B
Mater. Chem. Front., 2019, Advance Article

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    Dynamic covalent bonds: approaches from stable radical species

    D. Sakamaki, S. Ghosh and S. Seki, Mater. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QM00488B

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