4.8 Article

BN-substituted diphenylacetylene: a basic model for conjugated π-systems containing the BN bond pair

Journal

CHEMICAL SCIENCE
Volume 3, Issue 3, Pages 825-829

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00500f

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Funding

  1. American Chemical Society [48864-DNI1]
  2. National Science Foundation [DGE-0549503]
  3. Department of Energy, Office of Energy Efficiency and Renewable Energy [DE-PS36-03GO93013]
  4. DOE's Office of Biological and Environmental Research

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We report the synthesis, structural characterization, and optoelectronic properties of BN-Tolan 1 and Bis-BN-Tolan 2, one of the simplest conjugated systems containing the BN bond pair. BN-tolans 1 and 2 display absorption and emission properties that are distinct from their carbonaceous analogue, tolan. In addition, Bis-BN-Tolan 2 exhibits unique N-H/center dot center dot center dot pi(C C) hydrogen bonding in the solid state.

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