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Alternating diacetylene copolymer utilizing perfluorophenyl-phenyl interactions.

Rui Xu1, Volker Gramlich, Holger Frauenrath

  • 1Department of Materials, Eidgenössische Technische Hochschule Zürich, Hönggerberg, HCI H515, CH-8093 Zürich, Switzerland.

Journal of the American Chemical Society
|April 20, 2006
PubMed
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Researchers synthesized diacetylene monomers and achieved topochemical polymerization of a cocrystal. This resulted in a novel, strictly alternating poly(diacetylene) copolymer, showcasing the power of perfluorophenyl-phenyl interactions in crystal engineering.

Area of Science:

  • Organic Chemistry
  • Polymer Science
  • Crystallography

Background:

  • Diacetylenes are known for their topochemical polymerization in the solid state.
  • Supramolecular synthons play a crucial role in directing crystal packing and reactivity.

Purpose of the Study:

  • To investigate the topochemical polymerization of novel symmetric and unsymmetric diacetylene monomers.
  • To explore the use of perfluorophenyl-phenyl interactions for cocrystal formation and controlled polymerization.

Main Methods:

  • Synthesis of diacetylene monomers: 2,4-hexadiynylene dibenzoate (4), 2,4-hexadiynylene bis(pentafluorobenzoate) (5), and 6-(pentafluorobenzoyloxy)hexa-2,4-diynyl benzoate (6).
  • Cocrystallization of monomers 4 and 5 to form a 1:1 cocrystal (4.5).
  • Solid-state polymerization of the cocrystal 4.5.

Related Experiment Videos

  • Characterization using solid-state (13)C NMR, Raman spectroscopy, and single-crystal X-ray diffraction.

    • Main Results:

    • Successful synthesis of three distinct diacetylene monomers.
    • Formation of a 1:1 cocrystal (4.5) from two different diacetylene monomers.
    • Topochemical polymerization of the cocrystal 4.5 into a poly(diacetylene) copolymer (7).
    • Structural confirmation of the monomer-polymer cocrystal and the resulting copolymer.

    Conclusions:

    • Perfluorophenyl-phenyl interactions can be effectively utilized as complementary supramolecular synthons.
    • These interactions enable the cocrystallization of different diacetylene monomers.
    • This strategy leads to the unprecedented formation of a strictly alternating diacetylene copolymer via topochemical polymerization.