Get access

Highly Efficient Benzannulation of Poly(phenylene ethynylene)s

Authors

  • Hasan Arslan,

    1. Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY, 14853 (USA)
    Search for more papers by this author
  • Jonathan D. Saathoff,

    1. School of Chemical and Biomolecular Engineering, Cornell University, Ithaca, NY 14853 (USA)
    Search for more papers by this author
  • David N. Bunck,

    1. Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY, 14853 (USA)
    Search for more papers by this author
  • Prof. Dr. Paulette Clancy,

    Corresponding author
    1. School of Chemical and Biomolecular Engineering, Cornell University, Ithaca, NY 14853 (USA)
    • School of Chemical and Biomolecular Engineering, Cornell University, Ithaca, NY 14853 (USA)
    Search for more papers by this author
  • Prof. Dr. William R. Dichtel

    Corresponding author
    1. Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY, 14853 (USA)
    • Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY, 14853 (USA)
    Search for more papers by this author

  • This research was supported by the National Science Foundation (CHE-1124754). We also made use of the Cornell Center for Materials Research (CCMR) facilities with support from the NSF Materials Research Science and Engineering Centers (MRSEC) program (DMR-0520404). D.N.B. acknowledges the award of a Graduate Research Fellowship from the NSF. We acknowledge Fernando J. Uribe-Romo for help in preparing the graphical abstract.

Abstract

original image

Put a ring on it: Sterically congested polyarylenes can be synthesized by benzannulation reactions at each C[TRIPLE BOND]C bond of a poly(phenylene ethynylene) (see picture), one of the most easily synthesized and versatile classes of conjugated polymers. The benzannulation reaction is highly specific and efficient, as determined by an isotopic labeling study and several complementary spectroscopic methods.

Ancillary