The azulenic motif comprises fused 5- and 7-membered sp2-carbon rings and offers intriguing molecular design opportunities, particularly in the realm of molecular and optoelectronic applications. This presentation will introduce symmetric, linear 6,6’-biazulenic π-linkers symmetrically or asymmetrically terminated with isocyano and mercapto anchoring groups for heterobimetallic complexation and self-assembly on metallic gold surfaces. The phenomenon of half-wave (E1/2) potential compression/inversion upon two-electron reduction of the 6,6’-biazulenic moiety will be addressed in detail. A chemical strategy for stabilizing the radical-anion form of 6,6’-biazulenic derivatives that effectively suppresses their disproportionation into the corresponding neutral and closed-shell dianionic forms will be discussed. In addition to serving as a highly sensitive 13C NMR handle for quantifying electron delocalization mediated by the 6,6’-biazulenic π-bridge, the C4v-symmetric [(-NC)Cr(CO)5] unit proved to be an informative νN≡C/νC≡O Reflection-Absorption Infrared Spectroscopic (RAIRS) reporter in probing chemisorption of and electronic coupling across thiolate- and isocyanide-terminated 6,6’-biazulenes on Au(111).

Electron delocalization within and across linear 6,6’-biazulenic π-linkers

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.