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Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds

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Published in Angewandte Chemie: International Edition in English. 2015, vol. 54, no. 31, p. 8980-8983
Abstract Multicomponent surface architectures are introduced that operate with three different dynamic covalent bonds. Disulfide exchange under basic conditions accounts for the growth of π stacks on solid surfaces. Hydrazone exchange under acidic conditions is used to add a second coaxial string or stack, and boronic ester exchange under neutral conditions is used to co-align a third one. The newly introduced boronic ester exchange chemistry is compatible with stack and string exchange without interference from the orthogonal hydrazone and disulfide exchange. The functional relevance of surface architectures with three different dynamic covalent bonds is exemplified with the detection of polyphenol natural products, such as epigallocatechin gallate, in competition experiments with alizarin red. These results describe synthetic strategies to create functional systems of unprecedented sophistication with regard to dynamic covalent chemistry.
Keywords Boronic estersDynamic covalent chemistryHydrazonesMulticomponent systemsSupramolecular chemistry
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ZHANG, Kangda, MATILE, Stefan. Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds. In: Angewandte Chemie: International Edition in English, 2015, vol. 54, n° 31, p. 8980-8983. doi: 10.1002/anie.201503033 https://archive-ouverte.unige.ch/unige:74454

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Deposited on : 2015-08-03

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