Electrogenerated chemiluminescence. 75. Electrochemistry and ECL of 9,10-bis(2-naphthyl)anthracene

The spectroscopy, electrochemistry, and electrogenerated chemiluminescence (ECL) of 9,10-bis(2-naphthyl)anthracene (BNA) was investigated. BNA shows high fluorescence quantum yields (φ=0.86). Strong, intense ECL was observed on the surface of a Pt electrode in benzene + acetonitrile (1:1) while pulsing between the potentials for the first oxidization and reduction of BNA. The peak of ECL light emission was at 430 nm with an ECL efficiency about 90% of that of 9,10-diphenylanthracene (DPA). Cyclic voltammograms (CVs) of BNA show nernstian one-electron oxidations and reductions to the radical ions attributed to electron transfers to the anthracene core. The first reduction is followed by a second irreversible one-electron step and then two, closely spaced nernstian one-electron reductions assigned to electron transfer to the naphthalene moieties. The reduction CV was digitally simulated to establish the reduction mechanism.