The renaissance of dimercaptoarene chemistry in the context of functional materials has been driven, in part, by the quest to improve efficiency of molecular conductors and rectifiers. Azulene-containing molecular building blocks offer attractive design opportunities in this regard. Our group has recently reported on the first 2,6’-dimercaptoazulene linker, a motif which had been the subject of multiple theoretical studies relevant to molecular electronics. This presentation will introduce an inaugural 6,6’-biazulenic <i>π</i>-linker linearly terminated with mercapto junction groups at the 2,2’- positions of the biazulenic scaffold. A convenient synthetic access of this new dimercaptoarene on a gram scale, along with its spectroscopic, structural, and electrochemical characterization, will be presented. Similar to its 2,2’-isocyano-6,6’-biazulenic congener, the dithiol undergoes reversible two-electron reduction of the biazulenic core. The phenomenon of the half-wave (E<sub>1/2</sub>) potential inversion/compression occurring in this reduction process will be analyzed in detail. In addition, coordination and surface chemistry of the 2,2’-dimercapto-6,6’-biazulene linker will be discussed.

Synthesis, complexation and redox profile of the first biazulenic π-linker featuring mercapto termini

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

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