Abstract
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.
Original language | English (US) |
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Pages (from-to) | 15924-15926 |
Number of pages | 3 |
Journal | Journal of the American Chemical Society |
Volume | 132 |
Issue number | 45 |
DOIs | |
State | Published - Nov 17 2010 |