Synthesis and Verification of 9,10-Diphenylanthracene and Its Utility as a Fluorescer in a Peroxyoxalate Chemiluminescence System. An Organic Laboratory Project Integrating Synthesis with Fluorescence and Chemiluminescence

A project for the organic laboratory integrating the organic synthesis of 9,10-diphenylanthracene with fluorescence and chemiluminescence is described. The fluorescent compound is synthesized from anthraquinone by reaction with phenyllithium and subsequent hydrolysis and reduction with KI and NaH₂PO₂ in acetic acid. The structure of the product is verified by its melting point and by IR, ¹H NMR, and fluorescence spectroscopy. A peroxyoxalate chemiluminescent reaction using bis(2-butoxycarbonyl-3,4,6-trichlorophenyl) oxalate and hydrogen peroxide as the energy source is tested. The chemiluminescence emittance spectrum of the prepared diphenylanthracene is found to be essentially identical to that of the fluorescence spectrum of the same compound. Finally, the kinetics of the chemiluminescent reactions using different intensity-modifiers are monitored by measuring intensity-versus-time decay curves.