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Flow-IEG enables programmable thermodynamic properties in sequence-defined unimolecular macromolecules

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Abstract

Monodisperse oligomers are important intermediates for studying structure–property relationships in soft materials but are traditionally laborious to synthesize. A semi-automated synthetic system that combines the benefits of telescoped reactions in continuous flow with iterative exponential growth (IEG) greatly expedites this process and makes the rapid synthesis of structurally diverse oligomer libraries practical. Herein, the coupling chemistry in the Flow-IEG system has been upgraded and expanded to include both 1,4- and 1,5-triazole linkages between monomers through an improved copper-catalyzed azide–alkyne cycloaddition (CuAAC) and a newly-optimized ruthenium-catalyzed azide–alkyne cycloaddition (RuAAC), respectively. Improvements to the Flow-IEG framework enabled the library synthesis of monodisperse oligomers with variations in triazole connectivity. These discrete oligomers allowed the systematic evaluation of the consequences of triazole sequence on material properties. The crystallization properties of these macromolecules were highly dependent on both their monomer sequence and triazole substitution pattern.

Graphical abstract: Flow-IEG enables programmable thermodynamic properties in sequence-defined unimolecular macromolecules

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Publication details

The article was received on 19 Jul 2017, accepted on 29 Aug 2017 and first published on 05 Sep 2017


Article type: Paper
DOI: 10.1039/C7PY01204G
Citation: Polym. Chem., 2017, Advance Article
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    Flow-IEG enables programmable thermodynamic properties in sequence-defined unimolecular macromolecules

    A. C. Wicker, F. A. Leibfarth and T. F. Jamison, Polym. Chem., 2017, Advance Article , DOI: 10.1039/C7PY01204G

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