Sean Robertson | University of Ottawa | Université d'Ottawa (original) (raw)

Papers by Sean Robertson

I would like to begin by thanking my supervisor, Dr. Jaclyn Brusso; she is certainly the most pat... more I would like to begin by thanking my supervisor, Dr. Jaclyn Brusso; she is certainly the most patient person I know, and without her this thesis may not have come into existence. I would especially like to recognize her for her mentorship with the communication of both the science that I personally executed, and the science that captured my imagination. I want to acknowledge my colleagues in the Brusso lab, as well as my friends in Chemistry, individually; each of them was important to me. Nathan Yutronkie, who taught me the mysteries of butyl lithium; François Magnan (Mignon), for keeping it in the danger zone; Dr. Alicea Leitch, for her advice, her healthy skepticism, and her prodigious assistance with my first publication; Katie Harriman, my kindred spirit; Fatemah Habib, for convincing me to jump out of an airplane and for being an inspiring young scholar; Terry McCallum, for good times, especially on icy surfaces; Soofieh Afjeh, for her stabilizing presence; Mehak Patra, for various and sundry hilarities; Philip Bulsink, for his magnificent assistance with computational chemistry, without which I would still be combing through DFT error codes. I want to thank my brother and sister, Cameron and Alexa, for sharing their dreams of flight and for keeping me honest, respectively. My parents have my eternal gratitude; there is no way that I can ever repay them for their kindness and love, and the values and knowledge they have imparted to me. Finally, I would like to thank my wonderful partner, Ayesha Valliani. She was the wind in my sails, and she kept me afloat through the dark storms. Her presence in my life has meant the world to me.

The preparation and characterization of hexylated, brominated, and 5-hexyl-2-thienyl-substituted ... more The preparation and characterization of hexylated, brominated, and 5-hexyl-2-thienyl-substituted tetrathienoacridine (TTAc) is described. Comparative electrochemical, optical, computational, and solid-state studies with their thienoanthracene (TTAn) analogs demonstrate that replacement of CH with nitrogen leads to an overall lowering of the frontier molecular energy levels and decrease in the HOMO-LUMO energy gap. While the brominated TTAc and TTAn derivatives are isostructural, as indicated by X-ray diffraction studies, the lower sublimation temperature and thermochromic behaviour exhibited by bromo-TTAc is attributed to an additional dipole−dipole interaction resulting from the dipole moment afforded by carbon/nitrogen substitution in the core aromatic ring. This work represents a fundamental study of heteroatom substitution in 2-D conjugated small molecules and investigates how inclusion of an electron deficient aromatic ring into the molecular framework (i.e., acridine versus anthracene) can influence the physical properties.

I would like to begin by thanking my supervisor, Dr. Jaclyn Brusso; she is certainly the most pat... more I would like to begin by thanking my supervisor, Dr. Jaclyn Brusso; she is certainly the most patient person I know, and without her this thesis may not have come into existence. I would especially like to recognize her for her mentorship with the communication of both the science that I personally executed, and the science that captured my imagination. I want to acknowledge my colleagues in the Brusso lab, as well as my friends in Chemistry, individually; each of them was important to me. Nathan Yutronkie, who taught me the mysteries of butyl lithium; François Magnan (Mignon), for keeping it in the danger zone; Dr. Alicea Leitch, for her advice, her healthy skepticism, and her prodigious assistance with my first publication; Katie Harriman, my kindred spirit; Fatemah Habib, for convincing me to jump out of an airplane and for being an inspiring young scholar; Terry McCallum, for good times, especially on icy surfaces; Soofieh Afjeh, for her stabilizing presence; Mehak Patra, for various and sundry hilarities; Philip Bulsink, for his magnificent assistance with computational chemistry, without which I would still be combing through DFT error codes. I want to thank my brother and sister, Cameron and Alexa, for sharing their dreams of flight and for keeping me honest, respectively. My parents have my eternal gratitude; there is no way that I can ever repay them for their kindness and love, and the values and knowledge they have imparted to me. Finally, I would like to thank my wonderful partner, Ayesha Valliani. She was the wind in my sails, and she kept me afloat through the dark storms. Her presence in my life has meant the world to me.

The preparation and characterization of hexylated, brominated, and 5-hexyl-2-thienyl-substituted ... more The preparation and characterization of hexylated, brominated, and 5-hexyl-2-thienyl-substituted tetrathienoacridine (TTAc) is described. Comparative electrochemical, optical, computational, and solid-state studies with their thienoanthracene (TTAn) analogs demonstrate that replacement of CH with nitrogen leads to an overall lowering of the frontier molecular energy levels and decrease in the HOMO-LUMO energy gap. While the brominated TTAc and TTAn derivatives are isostructural, as indicated by X-ray diffraction studies, the lower sublimation temperature and thermochromic behaviour exhibited by bromo-TTAc is attributed to an additional dipole−dipole interaction resulting from the dipole moment afforded by carbon/nitrogen substitution in the core aromatic ring. This work represents a fundamental study of heteroatom substitution in 2-D conjugated small molecules and investigates how inclusion of an electron deficient aromatic ring into the molecular framework (i.e., acridine versus anthracene) can influence the physical properties.