Synthesis of Novel Pyrene and Isoindigo-Based Compounds for Electronic Applications

Abstract

In this thesis, we report the synthesis and characterization of new pyrene and isoindigo-based compounds that could be used in organic electronic applications. The performed reactions included various Suzuki-Miyaura coupling, nucleophilic aromatic substitution, and condensation reactions.

In Chapter 2, we report the synthesis of five novel isoindigo derivatives achieved through Suzuki coupling using either the respective boronic acid or boronic acid pinacol ester, in the presence of freshly synthesized Pd(PPh3)4 catalyst. Absorption and thermal properties were reported. Preliminary mesophase behavior of these molecules was studied in collaboration with Prof. S. Holger Eichhorn from the University of Windsor, and the X-ray structure of one of the compounds was determined by Dr. Jeanette Krause from the University of Cincinnati. Computational studies were performed by Prof. Brigitte Wex from the Lebanese American University.

In Chapter 3, we report the synthesis and characterization of two new pyrene derivatives that serve as potential building blocks for organic field-effect transistors (OFETs). The absorption properties of the isolated molecule are also reported.

In Chapter 4, we report the synthesis of two isoindigo dialdehyde derivatives, one of which was used in the synthesis of two novel covalent organic frameworks (COFs) that served as photocatalysts for the conversion of carbon dioxide into formate anions. The synthesis, characterization, and photocatalytic activity of the COFs were performed in collaboration with Prof. Dinesh Shetty from the Khalifah University of Science and Technology in Abu Dhabi, Prof. Ali Trabolsi from New York University in Abu Dhabi and Prof. Mohamad Hmadeh from the American University of Beirut.