The structure of azulene, an unusual nonbenzenoid aromatic hydrocarbon isomeric with naphthalene, involves an edge sharing combination of 5- and 7-membered sp2-carbon rings.  Very few mercaptoazulenes (or azulelyl thiols) are presently accessible and their interaction with transition metal atoms, ions or surfaces has not been explored.  Notably, a recent theoretical study concluded that the hitherto unknown 2,6-dimercaptoazulene motif should have a lower conductivity barrier in a wide bias range than 2,6-dimercaptonaphthalene (Bull. Mater. Sci., 2008  , 31, 353).  In this presentation, we will highlight syntheses and properties of several mercaptoazulenes, including 2,6-dimercapto-1,3-diethoxycarbonylazulene, and discuss our initial studies in coordination chemistry of azulenylthiolates.

Synthesis and coordination chemistry of mercapto- and dimercaptoazulenes

243rd National Meeting (2012)

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