Date of Award
Master of Science in Chemical Sciences (MSCB)
Graham S. Collier
Understanding structure-property relationships of underutilized p-conjugated chromophores is an important task for the continued discovery of materials that will find utility in organic electronic applications. Dihydropyrrolo[3,2-b]pyrroles (DHPPs) are synthetically simple and highly tailorable chromophores that can be decorated with diverse functionalities that readily manipulate optoelectronic properties useful for a variety of applications. However, a thorough understanding of how these functionalities influence properties of DHPPs that will be useful in applications such as electrochromism is unknown. Motivated to exploit the synthetic simplicity and tailorability of DHPPs, a family of DHPP chromophores was synthesized to probe how functionality and connectivity influence fundamental optoelectronic processes, such as absorbance and redox response. The overarching goal of this thesis is to understand the viability of manipulating optical transitions of doped DHPP chromophores and polymers. Investigations into optical and electrochemical properties reveal the ability to manipulate the redox activity and absorbance spectra of DHPP molecules and polymers as neutral and oxidized species such that control of the radical cation is achieved. The work described in this thesis presents design strategies for a new class of electron-rich chromophores and polymers that may find applicability as electrochromic materials. My findings demonstrate the ability to exploit the simple and tailorable synthesis of DHPPs to achieve solution-processible, high-contrast anodically coloring copolymers with tailored colors. This work lays the foundation for continued development of DHPP-based high-contrast, color-controlled electrochromic molecules and polymers for applications within organic electronics.
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