The Synthesis of Tunable Push-Pull Benzofulvene Monomers

Abstract

Researchers are increasingly aware of the unique optical properties and customizability of benzofulvenes, features that lend themselves to a variety of applications in optoelectronics and other fields. This research tested a simple and mild synthetic route, producing a wide range of functionalized benzofulvenes using phenyl indene intermediates. Benzofulvene structures were confirmed with NMR and optical data was collected using UV-vis spectroscopy and fluorimetry. It was found that strong electron push-pull systems, especially those involving a trifluoromethyl withdrawing group, experienced the most red-shifting. Solvents were also found to influence absorption wavelengths and emission intensity. Thus, benzofulvenes made with this method are tunable –­ substituents and solvents can easily be combined in unique ways to produce a variety of colors and fluorescence effects.