Modulation of Optoelectronic Properties of Electron Rich Pyrrolopyrroles via Peripheral Alterations
Disciplines
Chemistry | Organic Chemistry | Physical Sciences and Mathematics | Polymer Chemistry
Abstract (300 words maximum)
Understanding the structure-property relationship of pyridine-containing chromophores is important for the continued expansion of molecules possible for applications in organic electronic devices. Dihydropyrrolo[3,2-b]pyrroles (DHPPs) are synthetically simple and tailorable chromophores that can be manipulated for varying optoelectronic properties based on the functionalities of the starting materials. Several isomeric pyridine-containing DHPPs were synthesized to elucidate how subtle structural changes influenced the fundamental optoelectronic processes via ultraviolet-visible absorbance spectroscopy (UV-vis), cyclic voltammetry (CV), and differential pulse voltammetry (DPV). Initial investigations on the chromophores indicate that the position of the nitrogen within the pyridine does affect the optical properties of the oxidative species of the radical cation. These chromophores also exhibit halochromic responses in the presence of a strong acid. The chromophores were also used as a precursor to a palladium-catalyzed cross coupling Suzuki reaction. The resulting Π-extended isomeric DHPPs exhibit distinct electrochromic and halochromic responses but have minimal effect on the redox properties. This work aids in developing strategies to tailor optoelectronic properties with simple and tailorable DHPPs for varying applications of electronic devices.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Graham Collier
Modulation of Optoelectronic Properties of Electron Rich Pyrrolopyrroles via Peripheral Alterations
Understanding the structure-property relationship of pyridine-containing chromophores is important for the continued expansion of molecules possible for applications in organic electronic devices. Dihydropyrrolo[3,2-b]pyrroles (DHPPs) are synthetically simple and tailorable chromophores that can be manipulated for varying optoelectronic properties based on the functionalities of the starting materials. Several isomeric pyridine-containing DHPPs were synthesized to elucidate how subtle structural changes influenced the fundamental optoelectronic processes via ultraviolet-visible absorbance spectroscopy (UV-vis), cyclic voltammetry (CV), and differential pulse voltammetry (DPV). Initial investigations on the chromophores indicate that the position of the nitrogen within the pyridine does affect the optical properties of the oxidative species of the radical cation. These chromophores also exhibit halochromic responses in the presence of a strong acid. The chromophores were also used as a precursor to a palladium-catalyzed cross coupling Suzuki reaction. The resulting Π-extended isomeric DHPPs exhibit distinct electrochromic and halochromic responses but have minimal effect on the redox properties. This work aids in developing strategies to tailor optoelectronic properties with simple and tailorable DHPPs for varying applications of electronic devices.