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Protection-Group-Free Synthesis of Sequence-Defined Macromolecules via Precision λ-Orthogonal Photochemistry

Authors
  • Konrad, Waldemar
  • Fengler, Christian
  • Putwa, Sarrah
  • Barner-Kowollik, Christopher
Publication Date
May 20, 2019
Source
Queensland University of Technology ePrints Archive
Keywords
License
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Abstract

An advanced light-induced avenue to monodisperse sequence-defined linear macromolecules via a unique photochemical protocol is presented that does not require any protection-group chemistry. Starting from a symmetrical core unit, precision macromolecules with molecular weights up to 6257.10 g mol−1 are obtained via a two-monomer system: a monomer unit carrying a pyrene functionalized visible light responsive tetrazole and a photo-caged UV responsive diene, enabling an iterative approach for chain growth; and a monomer unit equipped with a carboxylic acid and a fumarate. Both light-induced chain growth reactions are carried out in a λ-orthogonal fashion, exciting the respective photosensitive group selectively and thus avoiding protecting chemistry. Characterization of each sequence-defined chain (size-exclusion chromatography (SEC), high-resolution electrospray ionization mass spectrometry (ESI-MS), and NMR spectroscopy), confirms the precision nature of the macromolecules.

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