Chem
Volume 1, Issue 1, 7 July 2016, Pages 114-126
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Article
Chemoselective Synthesis of Uniform Sequence-Coded Polyurethanes and Their Use as Molecular Tags

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Highlights

  • A facile method for preparing monodisperse sequence-defined polyurethanes is provided

  • Digitally coded polyurethanes are easy to read by tandem mass spectrometry sequencing

  • Sequence-coded polyurethanes can be used as tags to label various types of materials

The Bigger Picture

Product identification is an important topic in modern consumption societies. Indeed, the massive production of counterfeit goods leads to major economic losses and represents a threat to health and the environment. Thus, anti-counterfeiting technologies are crucial in many areas such as the pharmaceutical, cosmetics, food, and chemical industries. In particular, methods allowing product labeling at the nano or molecular scale are promising because they may not be easy to mimic. For example, synthetic polymers containing defined sequences of monomers can be used as molecular barcodes for product identification. Here, we report that digital sequences can be written at the molecular level on polyurethanes, which are cheap commodity plastics, using a very simple synthesis procedure. Moreover, the binary sequences formed can be easily deciphered by mass spectrometry. These coded polyurethanes can be used as molecular tags and blended in small amounts in other plastic materials.

Summary

Polyurethanes (PUs) constitute a popular class of plastic materials with a wide range of applications in construction, coatings, and the automotive industry. PUs are usually synthesized by step-growth polymerization and, therefore, exhibit non-uniform molecular structures. Here, we show that uniform PUs can be prepared by a facile chemoselective multistep-growth approach. This strategy permits precise control of the chain lengths of the PUs formed and their primary structure, thus making the preparation of coded monomer sequences possible. Furthermore, it was found that these polymers are remarkably easy to analyze by tandem mass spectrometry sequencing. Thus, these precision polymers can potentially be used as molecular barcodes in various applications. As a proof of concept, their use as anti-counterfeiting tags for identification of materials is reported here.

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