Isoindigo and NDI derivatives : promising building blocks for organic electronics.

Abstract

We report the synthesis and characterization of a series of isoindigo-based and naphtalene diimide (NDI)-based organic materials as promising building blocks for different fields of organic electronics including organic photovoltaics (OPVs) and organic field effect transistors (OFETs). The synthesis of these compounds was carried out through three steps via condensation, nucleophilic aromatic substitution and Suzuki coupling reactions. In Chapter 2, we present the synthesis of six new isoindigo-based small molecules as potential molecules for OPVs and OFETs. We report the effect of altering the substituent on the photophysical and thermal properties. In Chapter 3, we report DFT calculations and electrochemistry of isoindigo-based molecules in effort to provide a better understanding of the substituent effects on the energy levels. This chapter was done in collaboration with Prof. Brigitte Wex from the Lebanese American University and aims to offer better insight to the design of small molecules for electronic applications. In Chapter 4, we report the synthesis of two new isoindigo-based small molecules as precursors for covalent organic framework (COF) materials. The synthesis of isoindigo dialdehydes were prepared in our laboratory whereas the COF materials were done by the work of Prof. Ali Trabolsi from the New York University in Abu Dhabi. Finally, Chapter 5 discusses the synthesis of three NDI-based molecules for electronic applications. It provides understanding of the effect of the substituent through photophysical, thermal and computational studies.