期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 14, 页码 3413-3419出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201705939
关键词
convergent; multicomponent reactions; photochemistry; sequence control; sequence-defined macromolecules
资金
- German Research Council (DFG) [SFB 1176]
- Australian Research Council (ARC)
- Science and Technology of Nanosystems (STN) program of the Helmholtz association
- VCI
- Queensland University of Technology (QUT)
We introduce the convergent synthesis of linear monodisperse sequence-defined oligomers through a unique approach, combining the Passerini three-component reaction (P-3CR) and a Diels-Alder (DA) reaction based on photocaged dienes. A set of oligomers is prepared resting on a Passerini linker unit carrying an isocyano group for chain extension by P-3CR and a maleimide moiety for photoenol conjugation enabling a modular approach for chain growth. Monodisperse oligomers are accessible in a stepwise fashion by switching between both reaction types. Employing sebacic acid as a core unit allows the synthesis of a library of symmetric sequence-defined oligomers. The oligomers consist of alternating P-3CR and photoblocks with molecular weights up to 3532.16 g mol(-1), demonstrating the successful switching from P-3CR to photoenol conjugation. In-depth characterization was carried out including size-exclusion chromatography (SEC), high-resolution electrospray ionization mass spectrometry (ESI-MS) and NMR spectroscopy, evidencing the monodisperse nature of the precision oligomers.
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