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A Scalable and High‐Yield Strategy for the Synthesis of Sequence‐Defined Macromolecules
Author(s) -
Solleder Susanne C.,
Zengel Deniz,
Wetzel Katharina S.,
Meier Michael A. R.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509398
Subject(s) - macromolecule , chemistry , monomer , sequence (biology) , yield (engineering) , combinatorial chemistry , metathesis , mass spectrometry , olefin metathesis , stereochemistry , organic chemistry , polymerization , materials science , chromatography , polymer , biochemistry , metallurgy
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).