Simplified Synthesis of Conjugated Polymers Enabled via 1,4-Dihydropyrrolo[3,2-b]pyrrole
type: CreativeWork
description: Conjugated polymers have attracted significant attention as the active layer material in organic electronics, such as organic photovoltaics and light-emitting diodes, partly due to the ability to influence a broad range of properties through structural design motifs. However, high performance conjugated polymers suffer from numerous synthetic steps, generation of toxic waste, and harsh reaction conditions all of which impart additional costs that inhibit their widespread utilization. Therefore, an emphasis on reducing synthetic complexity and utilizing abundant, commercially available starting materials is needed for organic electronics to reach their full potential. Dihydropyrrolo[3,2-b]pyrrole (H2DPP) chromophores offer a simple one-pot synthesis to access electron-rich scaffolds for incorporation into a new class of conjugated polymers with tunable optoelectronic properties. Motivated by the simple synthesis, ease of purification, and an overall lower synthetic complexity for accessing monomers, dihalogenated H2DPP monomers are synthesized and subsequently polymerized with electron-rich and electron-deficient comonomers. Through the choice of comonomers, H2DPP polymers demonstrate facile optical tunability, evident by absorbance and fluorescence across the visible spectrum. Additionally, polymers demonstrate suitable thermal stability for standard processing protocols and motivate exploration of film properties. The synthetic complexity of the resulting polymers also is calculated and H2DPP copolymers are quantified to be synthetically simpler compared to many conventional polymers used in solid-state and electrochemical applications. In total, this work shows that the incorporation of H2DPP into polymeric materials simplifies the synthesis of conjugated polymers, maintains tailorability through functionality and comonomer choice, and lays the foundation for the continued development of a novel class of organic electronic materials.
abstract: Conjugated polymers have attracted significant attention as the active layer material in organic electronics, such as organic photovoltaics and light-emitting diodes, partly due to the ability to influence a broad range of properties through structural design motifs. However, high performance conjugated polymers suffer from numerous synthetic steps, generation of toxic waste, and harsh reaction conditions all of which impart additional costs that inhibit their widespread utilization. Therefore, an emphasis on reducing synthetic complexity and utilizing abundant, commercially available starting materials is needed for organic electronics to reach their full potential. Dihydropyrrolo[3,2-b]pyrrole (H2DPP) chromophores offer a simple one-pot synthesis to access electron-rich scaffolds for incorporation into a new class of conjugated polymers with tunable optoelectronic properties. Motivated by the simple synthesis, ease of purification, and an overall lower synthetic complexity for accessing monomers, dihalogenated H2DPP monomers are synthesized and subsequently polymerized with electron-rich and electron-deficient comonomers. Through the choice of comonomers, H2DPP polymers demonstrate facile optical tunability, evident by absorbance and fluorescence across the visible spectrum. Additionally, polymers demonstrate suitable thermal stability for standard processing protocols and motivate exploration of film properties. The synthetic complexity of the resulting polymers also is calculated and H2DPP copolymers are quantified to be synthetically simpler compared to many conventional polymers used in solid-state and electrochemical applications. In total, this work shows that the incorporation of H2DPP into polymeric materials simplifies the synthesis of conjugated polymers, maintains tailorability through functionality and comonomer choice, and lays the foundation for the continued development of a novel class of organic electronic materials.
author: Bell, Kenneth-John Jack
keywords: Conjugated Polymers, Simple Synthesis, Pyrrolopyrrole, Polymerization, Direct (Hetero)arylation Polymerization, Chemistry, Organic Chemistry, Polymer and Organic Materials, Polymer Chemistry, Semiconductor and Optical Materials
date published: 2022-04-22T07:00:00Z
date modified: 2026-07-24T02:43:51Z
provider: Kennesaw State University
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: Kennesaw State University