Bis-benzofulvenes: Synthesis and Studies on Their Optoelectronic Properties.

We report the synthesis of bis-benzofulvenes and the studies on their optical and redox properties. Bis-benzofulvenes were achieved through the Pd-catalyzed intramolecular Heck coupling followed by Ni-mediated C(sp)-Br dimerization. Low optical and electrochemical energy gaps of 2.05 and 1.68 eV were achieved by tuning the substituent on the exomethylene unit and the aromatic ring. The observed trends in the energy gaps were compared, and the frontier molecular orbitals were visualized using the density functional theory.