Welch, GregoryCann, Jonathan Robert2021-05-142021-05-142021-05-12Cann, J. R. (2021). Developing Structure-Property Relationships for N-Annulated Perylene Diimides (Doctoral thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca.http://hdl.handle.net/1880/113410This thesis presents structure-property relationships of a series of functionalized N-annulated perylene diimide chromophores. Chapter one introduces the perylene diimide (PDI) chromophore and covers functionalization through bay annulation. Chapter two of this thesis explores the impact of electron deficient nitro groups on N-annulated PDI (NPDI) and further evaluates the impact of varied alkyl substituents (M2-M4). Chapter three explores a set of NPDI dimers and the importance of the dihedral angle between the two fragments (M5-M7). Chapter four explores the modified the optical and electronic properties of M7 by incorporating small organic chromophores between the two halves of the NPDI dimer (M8-M10). Chapter five explores derivatives of the NPDI where small electron rich aryl groups have been appended to the periphery (M11-M15). Finally, in chapter six a pair of highly related NPDI tetramers (M17, M17) are examined and found to have unusually disparate properties. Each of these derivatives was characterized by 1H NMR, CV, UV-Vis absorption and emission as well as X-Ray crystallography and spectroelectrochemistry as needed.engUniversity of Calgary graduate students retain copyright ownership and moral rights for their thesis. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission.Perylene DiimideStructure Property RelationshipChemistrySynthesisEnergyEngineering--Chemicaldoctoral thesis10.11575/PRISM/38864