Your browser does not fully support modern features. Please upgrade for a smoother experience.
Dynamic Covalent Chemistry: History
Please note this is an old version of this entry, which may differ significantly from the current revision.
Contributor: Yu Peng

Dynamic covalent chemistry (DCC) designates a chemical paradigm in which molecular components are linked through covalent bonds that undergo reversible cleavage and reformation under conditions permitting thermodynamic equilibration [1]. The field was formally named by Rowan and co-workers in 2002 to describe systems that combine the robustness of covalent linkages with the error-correcting and adaptive capacity characteristic of reversible noncovalent interactions [2][3]. Within supramolecular chemistry and organic chemistry, the defining operational feature of DCC is that the bond-forming and bond-breaking processes are continuously active and responsive to external parameters such as temperature, solvent, pH, and concentration, so that the distribution of products reflects the thermodynamic minimum accessible under the chosen conditions [1]. This equilibration enables self-correction, self-sorting, and template-directed assembly, allowing simple building blocks to be converted into structurally complex architectures—including macrocycles, cages, and interlocked molecules—that would be difficult to obtain through kinetically controlled stepwise synthesis [1][3]. The dynamic covalent bonds most commonly employed include imines, disulfides, boronic esters, and acylhydrazones, each characterized by a distinct exchange mechanism and kinetic profile [1]. The term thus denotes the design logic—spanning bond selection, exchange kinetics, and equilibrium control—through which reversible covalent linkages are exploited to generate adaptive molecular systems under thermodynamic control [4].

  • Reversible covalent bond
  • thermodynamic equilibrium
  • self-sorting
  • dynamic combinatorial library
  • error correction

Supramolecular Chemistry and Complexes·Organic Chemistry·Chemistry·Physical Sciences

References

  1. Elarbi Chatir; Arthur H. G. David; Adèle Gapin; Antoine Goujon; Dynamic Covalent Synthesis Applied to Optoelectronic and Energy Materials: Design, Applications and Limitations. Eur. J. Org. Chem. 2024, 27, e202400211, 10.1002/ejoc.202400211.
  2. Jonathan R. Nitschke; Supramolecular and dynamic covalent reactivity. Chem. Soc. Rev. 2014, 43, 1798-1799, 10.1039/c4cs90006e.
  3. Fabien B. L. Cougnon; Artur R. Stefankiewicz; Sébastien Ulrich; Dynamic covalent synthesis. Chem. Sci. 2023, 15, 879-895, 10.1039/d3sc05343a.
  4. Yinghua Jin; Chao Yu; Ryan J. Denman; Wei Zhang; Recent advances in dynamic covalent chemistry. Chem. Soc. Rev. 2013, 42, 6634-6654, 10.1039/c3cs60044k.
More
This entry is offline, you can click here to edit this entry!
Write an Entry