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Published on: February 6, 2020
De Novo Labile C-N Bonds Enable Dynamic Covalent Chemistry and Reversible Bioimaging
Chenming Chan1, Yating Wang1, Jingjing Wan1
1Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241, China.
None:
Dynamic covalent bonds (DCBs) enable reversible bond formation/cleavage, offering exciting possibilities for smart and adaptive materials, yet challenges such as slow kinetics and stringent conditions required for the reverse reaction currently hinder their broader use. We present a novel C-N σ-bond with exceptional reversibility and ultrafast kinetics (t1/2 = 200 ms) across diverse primary aliphatic amine substrates, occurring spontaneously under ambient conditions without catalysts or external energy input, which is enabled by remarkably low activation barriers and near-equilibrium energetics. We showcase this transformative DCB's versatility in reversible gas-fixation, programmable transamination, and construct the first reversible chemical probes for real-time quantitative tracking of spatiotemporal histamine dynamics in live cells and in vivo within the brain under inflammatory pathology. This work redefines C-N σ-bonds as dynamic linkages, opening avenues for innovation in organic chemistry, adaptive materials, and dynamic biosystems.
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