The polar nonbenzenoid aromatic framework of azulene involves an edge sharing combination of 5- and 7-membered carbon rings. While the chemistry of azulene is dominated by derivatization at the 1,3-positions of the azulenic nucleus, we have recently engaged in the quest for a novel class of metal-organic architectures involving the 2,6-azulenic framework. This presentation will highlight recent developments in the chemistry of azulenic scaffolds featuring mercapto, cyano and isocyano functionalization along their molecular axis. In particular, strategies for controlled orientation of the molecular dipole in organometallic systems containing asymmetric azulenic and biazulenic units will be presented. The use of nitrile and isonitrile infrared reporters for monitoring formation and reactivity of azulenic SAMs on metallic gold will be discussed as well.

New developments in the coordination and surface chemistry of azulenic and linear biazulenic motifs functionalized along their molecular axis

245th National Meeting (2013)

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