Solution Processable Perylene Diimide Materials for Photovoltaic and Photonic Applications

Date
2022-06
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Abstract
This thesis discusses the investigation of the modification of perylene diimide materials to enable solution processing from non-halogenated solvents. Chapter one of this thesis will introduce the concept of organic semiconduction materials and their implementation in organic photovoltaics and the solution fabrication processes associated with their production. Chapter two discusses the synthesis and aliphatic sidechain engineering of perylene diimide-diketopyrrolopyrrole-perylene diimide (E1) materials to enable solubility and solution processability within non-halogenated solvents. In chapter three, the N-annulated perylene diimide dimer (tPDI2N-EH, E6) was prepared on a multi-gram scale. The dimer framework was derivatized via sidechain engineering with functional functionalism sidechains (E7-E13) to facilitate interactions to improve organic photovoltaic performance. The champion performing material (E6) was applied to the solution fabrication of optical filters in a collaborative project to promote photosynthetic activity. In chapter four, a monomeric N-annulated perylene diimide was modified with thermally labile protecting group tert-butyloxycarbonyl (Boc), enabling solubility in non-halogenated solvents. Thermal annealing in the solid-state yields a solvent-resistant material applied as an electron transporting material in the hybrid electron transporting layers within organic photovoltaics. Finally, chapter five explores the molecular engineering of electron-transporting materials comprising perylene diimide- Indacenodithiophene-perylene diimide (E15-E16) molecular frameworks. The implications of molecular engineering with respect to the material's optoelectronic properties are discussed. The materials were evaluated as electron transport materials within organic photovoltaic devices.
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Keywords
Organic Photovoltaics, Perylene Diimide
Citation
Cieplechowicz, E. (2022). Solution processable perylene diimide materials for photovoltaic and photonic applications (Doctoral thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca.