title: A Scalable and High-Yield Strategy for the Synthesis of Sequence-Defined Macromolecules.
abstract: The efficient synthesis of a sequence-defined decamer, its characterization, and its straightforward dimerization through self-metathesis are described. For this purpose, a monoprotected AB monomer was designed and used to synthesize a decamer bearing ten different and selectable side chains by iterative Passerini three-component reaction (P-3CR) and subsequent deprotection. The highly efficient procedure provided excellent yields and allows for the multigram-scale synthesis of such perfectly defined macromolecules. An olefin was introduced at the end of the synthesis, allowing the self-metathesis reaction of the resulting decamer to provide a sequence-defined 20-mer with a molecular weight of 7046.40 g mol(-1). The obtained oligomers were carefully characterized by NMR and IR spectroscopy, GPC and GPC coupled to ESI-MS, and mass spectrometry (FAB and orbitrap ESI-MS).
authors.affiliation: Institut für Organische Chemie, Karlsruhe Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Susanne C
authors.initials: SC
authors.lastname: Solleder
authors.affiliation: Institut für Organische Chemie, Karlsruhe Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Deniz
authors.initials: D
authors.lastname: Zengel
authors.affiliation: Institut für Organische Chemie, Karlsruhe Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Katharina S
authors.initials: KS
authors.lastname: Wetzel
authors.affiliation: Institut für Organische Chemie, Karlsruhe Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany. m.a.r.meier@kit.edu.
authors.forename: Michael A R
authors.initials: MA
authors.lastname: Meier
keywords: Passerini reaction; metathesis; multicomponent reactions; polymers; sequence control