Expanded Indenofluorenes: From Structure to Theory

Abstract

As humanity moves into the future, the demand for new electronic devices increases. Flexible electronics that could be bendable, wearable, and/or biocompatible are more desired and, fortunately, closer to our grasp than ever. In order to produce these new devices, electronic materials not based on ridged, brittle crystals are needed. One candidate for these new electronics are organic electronic materials. Organic electronic materials have the potential to lead to devices that are flexible, simple to produce and that can take advantage of state-of-the-art processes like non-linear optics, spintronics and singlet fission. In order to access these exciting new devices, however, a better understanding of the type of conjugated organic molecules on which they will be based is needed.

This dissertation explores the expansion of the indenofluorene project from a rotation student’s small spin off to an examination of a full class of materials. First, this document details the synthesis of donor-acceptor-donor triads using indenofluorene starting material, the dione, as the acceptor portion. What follows is an in-depth examination of the aromatic and antiaromatic properties of the class of materials we deemed diarenoantiaromatics. The computational techniques used are expanded along with the antiaromatic core of each molecule in order to evaluate the diradical character of the core expanded molecules being synthesized by my lab mates. Finally, the synthesis and characterization of a nine ring, linear dianthracenoindacene and the progress toward the thirteen ring dipentacenoindacene isomers are described.