Synthèse de composés à caractère biradicalaire et extension du système conjugué de l'anthanthrone

Authors: Boismenu-Lavoie, Joël
Advisor: Morin, Jean-François
Abstract: Due to their inherent reactivity, biradical compounds synthesis is hard, limiting their uses in many applications such as non-linear optics and organic electronics. Their interesting properties arise from the equilibrium between their close-shell electronic structure, where valence orbital electrons are paired, and their open-shell state, where those electrons are located in two different orbitals. The main strategy used to obtain those compounds is based on Clar’s sextets generation, which increases the system’s aromaticity when adopting the close shell conformation. While effective, this method usually produces rigid molecules whose biradical character only appears at a given temperature. Our strategy is to force our compound to adopt a biradical structure by using steric hindrance as the driving force rather than the aromatic stabilization. By breaking the π component of a double bond, it gains a simple bond character, making it easier for the molecule to rearrange itself in a sterically less energetic conformation. The main goal of this project is to expand the 4,10-dibromoanthanthrone π-system conjugation in order to modify its optic and electronic properties, and generate biradical compounds. In addition to its fully conjugated structure, this molecule is very large, generating an important steric hindrance. This strategy is discussed in this manuscript and biradical character is observed on multiple compounds, revealed by temperature augmentation in solution and pressure application in solid phase.
Document Type: Mémoire de maîtrise
Issue Date: 2018
Open Access Date: 24 April 2018
Permalink: http://hdl.handle.net/20.500.11794/28318
Grantor: Université Laval
Collection:Thèses et mémoires

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