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Chemistry. 2013 Jul 15;19(29):9506-10. doi: 10.1002/chem.201301446. Epub 2013 Jun 10.

A new dynamic covalent bond of Se-N: towards controlled self-assembly and disassembly.

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Key Lab of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing 100084, P.R. China.


A new kind of Se-N dynamic covalent bond has been found that can form between the Se atom of a phenylselenyl halogen species and the N atom of a pyridine derivative, such as polystyrene-b-poly(4-vinylpyridine). This Se-N dynamic covalent bond can be reversibly and rapidly formed or cleaved under acidic or basic conditions, respectively. Furthermore, the bond can be dynamically cleaved by heating or treatment with stronger electron-donating pyridine derivatives. The multiple responses of Se-N bond to external stimuli has enriched the existing family of dynamic covalent bonds. It can be used for controlled and reversible self-assembly and disassembly, which may find potential applications in a number of areas, including self-healing materials and responsive assemblies.


NMR spectroscopy; block copolymer; covalent bond; selenium; self-assembly


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