ArticleProceedings of the National Academy of Sciences of the United States of America2022
Single-crystal-to-single-crystal translation of a helical supramolecular polymer to a helical covalent polymer.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed, 37 citations in OpenAlex.
- A hydroxyl group dictates handedness, pitch, and mechanics in a crystalline covalent helical polymer.Science advances · 2025Article
- The Ascent of Supramolecular Polymers and Gels in Asymmetric Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Topochemical synthesis of chiroptical materials through charge-transfer/Diels-Alder cascade reaction.Nature communications · 2025Article
- Topochemical Ring-Opening Polymerization of an Oxathianethione.Journal of the American Chemical Society · 2025Article
- Endowing single-crystal polymers with circularly polarized luminescence.Nature communications · 2025Article
- Hierarchical single-crystal-to-single-crystal transformations of a monomer to a 1D-polymer and then to a 2D-polymer.Nature communications · 2024Article
- Simultaneous and in situ syntheses of an enantiomeric pair of homochiral polymers as their perfect stereocomplex in a crystal.Nature communications · 2024Article
- Rational design and topochemical synthesis of polymorphs of a polymer.Chemical science · 2023Article
- Single-crystal-to-single-crystal translation of a helical supramolecular polymer to a helical covalent polymer.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Polymers possessing helical conformation in the solid state are in high demand. We report a helical peptide-polymer via the topochemical ene-azide cycloaddition (TEAC) polymerization. The molecules of the designed Gly-Phe-based dipeptide, decorated with ene and azide, assemble in its crystals as β-sheets and as supramolecular helices in two mutually perpendicular directions. While the NH…O H-bonding facilitates β-sheet-like stacking along one direction, weak CH…N H-bonding between the azide-nitrogen and vinylic-hydrogen of molecules belonging to the adjacent stacks arranges them in a head-to-tail manner as supramolecular helices. In the crystal lattice, the azide and alkene of adjacent molecules in the supramolecular helix are suitably preorganized for their TEAC reaction. The dipeptide underwent regio- and stereospecific polymerization upon mild heating in a single-crystal-to-single-crystal fashion, yielding a triazoline-linked helical covalent polymer that could be characterized by single-crystal X-ray diffraction studies. Upon heating, the triazoline-linked polymer undergoes denitrogenation to aziridine-linked polymer, as evidenced by differential scanning calorimetry, thermogravimetric analysis, and solid-state NMR analyses.
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