The key step in accessing the title species (5), the first nonbenzenoid diisocyanobiaryl, involved an unexpected homocoupling of a 6-bromoazulene derivative. The reversible 2e- reduction of 5 was addressed electrochemically and computationally. The shifts in energies of the S 0→S1 and S0→S2 transitions for a series of related 6,6′-biazulenyl derivatives correlate with the e--donating/-withdrawing strength of their 2,2′-substituents but follow opposite trends. Species 5 adsorbs end-on (η1) to the Au(111) surface via one of its -NC groups to form a 2-nm-thick film. In addition, bimetallic coordination of 5's -NC termini can be readily achieved. © 2010 American Chemical Society.
CITATION STYLE
Maher, T. R., Spaeth, A. D., Neal, B. M., Berrie, C. L., Thompson, W. H., Day, V. W., & Barybin, M. V. (2010). Linear 6,6′-biazulenyl framework featuring isocyanide termini: Synthesis, structure, redox behavior, complexation, and self-assembly on Au(111). Journal of the American Chemical Society, 132(45), 15924–15926. https://doi.org/10.1021/ja108202d
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