Synthesis and Properties of Regioisomeric Donor-Acceptor Chromophores Based on Pyrene Quinones

Abstract

The synthesis and study of new organic molecules for applications in organic electronics is a growing field within the chemical sciences. Research in our group attempts to address a particular need for small-molecules that can function as n-type organic semiconductors, which transport electrons in organic electronic devices such as organic photovoltaic cells (OPVs) or organic field effect transistors (OFETs). Not only is there a general lack in the number of new n-type molecules in the literature, but there are even fewer examples of these electron-poor molecules that also have the capability to absorb light in the visible and near infrared region of the solar spectrum in order to contribute to the overall efficiency in an organic photovoltaic cell. The goal of the work in this thesis was to design new electron-poor molecules based on pyrene quinones and their derivatives, and to investigate the structure-property relationships that lead to optimal energy levels, light absorption, and long-range ordering of the molecules in the solid state. Using the donor-acceptor approach, a series of new chromophores was synthesized with pyrene quinones as the central acceptor moieties and N,N-dialkyl-4-ethynyl aniline substituents as the donor portions. By varying the substitution pattern of donor and acceptor portions around the pyrene ring, and the strength of the acceptor moiety, important structure property relationships were discovered.