Substituted Diarylnorbornadienes and Quadricyclanes: Synthesis, Photochemical Properties, and Effect of Substituent on the Kinetic Stability of Quadricyclanes.

In this Article, we present a new method for the synthesis of diarylnorbornadiene derivatives. Through the use of a two-step procedure consisting of a tandem alkene insertion-Suzuki coupling reaction followed by a DDQ dehydrogenation, we have been able to synthesize derivatives with a wide variety of substituents. We also present the results of UV-visible spectroscopy studies and kinetics experiments that show the effect of substituent on light absorption properties of the norbornadienes as well as the kinetic stability of the quadricyclanes that result from their photochemical conversion.