All Publications


  • Mechanochemical synthesis of an elusive fluorinated polyacetylene. Nature chemistry Boswell, B. R., Mansson, C. M., Cox, J. M., Jin, Z., Romaniuk, J. A., Lindquist, K. P., Cegelski, L., Xia, Y., Lopez, S. A., Burns, N. Z. 2020

    Abstract

    Polymer mechanochemistry has traditionally been employed to study the effects of mechanical force on chemical bonds within a polymer backbone or to generate force-responsive materials. It is under-exploited for the scalable synthesis of wholly new materials by chemically transforming the polymers, especially products inaccessible by other means. Here we utilize polymer mechanochemistry to synthesize a fluorinated polyacetylene, a long-sought-after air-stable polyacetylene that has eluded synthesis by conventional means. We construct the monomer in four chemical steps on gram scale, which involves a rapid incorporation of fluorine atoms in an exotic photochemical cascade whose mechanism and exquisite stereoselectivity were informed by computation. After polymerization, force activation by ultrasonication produces a gold-coloured, semiconducting fluoropolymer. This work demonstrates that polymer mechanochemistry is a valuable synthetic tool for accessing materials on a preparative scale.

    View details for DOI 10.1038/s41557-020-00608-8

    View details for PubMedID 33349696

  • Multireference computations elucidate the mechanism of a photochemical cascade reaction towards fluoropolyacetylene Corzo, H., Boswell, B., Burns, N., Lopez, S. AMER CHEMICAL SOC. 2019
  • Xenon Difluoride Mediated Fluorodecarboxylations for the Syntheses of Di- and Trifluoromethoxyarenes ORGANIC LETTERS Chatalova-Sazepin, C., Binayeva, M., Epifanov, M., Zhang, W., Foth, P., Amador, C., Jagdeo, M., Boswell, B. R., Sammis, G. M. 2016; 18 (18): 4570–73

    Abstract

    XeF2 is demonstrated to be a more proficient fluorine-transfer reagent than either NFSI or Selectfluor in fluorodecarboxylations of both mono- and difluoroaryloxy acetic acid derivatives. This method efficiently converts a wide range of neutral and electron-poor substrates to afford the desired di- and trifluoromethyl aryl ethers in good to excellent yields. The purifications are facile, and the reaction times are less than 5 min, which makes these fluorodecarboxylations promising for future PET-imaging applications.

    View details for DOI 10.1021/acs.orglett.6b02208

    View details for Web of Science ID 000383640600032

    View details for PubMedID 27560791