Linear 6,6′-biazulenyl framework featuring isocyanide termini: Synthesis, structure, redox behavior, complexation, and self-assembly on Au(111)

Tiffany R. Maher, Andrew D. Spaeth, Brad M. Neal, Cindy L. Berrie, Ward H. Thompson, Victor W. Day, Mikhail V. Barybin

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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 languageEnglish (US)
Pages (from-to)15924-15926
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number45
DOIs
StatePublished - Nov 17 2010

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