Biosourced Monomers: Toward Sustainable Conjugated Polymers for Organic Electronics

Boivin, L P; Dupont, William; Gendron, David; Leclerc, Mario

doi:10.1002/macp.202200378

Cited by 10 publications

(3 citation statements)

References 113 publications

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“…Furans have been used to prepare various monomers for polymerizations, including π-conjugated polymers. , For example, Baillargeon and co-workers synthesized lignocellulosic furfuryl biobased diacetylenes and generated polydiacetylenes via topochemical polymerization. Vanillin is another exemplary biobased organic monomer that is used for synthesizing π-conjugated materials for organic light-emitting diodes, and others, , with notable contributions from Leclerc, and Arndstsen, among others. The chemical composition of this monomer, which includes substantial conjugation and synthetically transformable functional groups, enables its ability to be used in the creation of π-conjugated polymers with degradable, labile chemical sites.…”

Section: π-Conjugated Monomersmentioning

confidence: 99%

Degradable π-Conjugated Polymers

Uva,

Michailovich,

Hsu

et al. 2024

J. Am. Chem. Soc.

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The integration of next-generation electronics into society is rapidly reshaping our daily interactions and lifestyles, revolutionizing communication and engagement with the world. Future electronics promise stimuli-responsive features and enhanced biocompatibility, such as skin-like health monitors and sensors embedded in food packaging, transforming healthcare and reducing food waste. Imparting degradability may reduce the adverse environmental impact of next-generation electronics and lead to opportunities for environmental and health monitoring. While advancements have been made in producing degradable materials for encapsulants, substrates, and dielectrics, the availability of degradable conducting and semiconducting materials remains restricted. π-Conjugated polymers are promising candidates for the development of degradable conductors or semiconductors due to the ability to tune their stimuli-responsiveness, biocompatibility, and mechanical durability. This perspective highlights three design considerations: the selection of π-conjugated monomers, synthetic coupling strategies, and degradation of π-conjugated polymers, for generating π-conjugated materials for degradable electronics. We describe the current challenges with monomeric design and present options to circumvent these issues by highlighting biobased π-conjugated compounds with known degradation pathways and stable monomers that allow for chemically recyclable polymers. Next, we present coupling strategies that are compatible for the synthesis of degradable π-conjugated polymers, including direct arylation polymerization and enzymatic polymerization. Lastly, we discuss various modes of depolymerization and characterization techniques to enhance our comprehension of potential degradation byproducts formed during polymer cleavage. Our perspective considers these three design parameters in parallel rather than independently while having a targeted application in mind to accelerate the discovery of next-generation high-performance πconjugated polymers for degradable organic electronics.

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Section: π-Conjugated Monomersmentioning

confidence: 99%

Degradable π-Conjugated Polymers

Uva,

Michailovich,

Hsu

et al. 2024

J. Am. Chem. Soc.

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show abstract

“…[1][2][3][4][5] The applications in organic electronics, such as organic thin-film transistors (OTFTs), have driven scientific researchers to continuously explore high-performance CPs. [6][7][8][9][10][11][12][13] CPs exhibit good DOI: 10.1002/macp.202300220 charge transport performances originated from the strong intermolecular 𝜋-orbital overlap as well as enhanced interchain interactions. [14][15][16][17] Quinoidal compounds are well known as a unique chemical structure with doublebond connection between the units, resulting in an extended 𝜋-electron delocalization and an improved backbone planarity.…”

Section: Introductionmentioning

confidence: 99%

“…[ 1–5 ] The applications in organic electronics, such as organic thin‐film transistors (OTFTs), have driven scientific researchers to continuously explore high‐performance CPs. [ 6–13 ] CPs exhibit good charge transport performances originated from the strong intermolecular π‐orbital overlap as well as enhanced interchain interactions. [ 14–17 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Conjugated Polymers Based on Thieno[3,4‐b]Thiophene Quinoidal Unit

Shao,

He,

Wang

et al. 2023

Macro Chemistry & Physics

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Driven by the success of quinoidal units for enabling high performance polymer semiconductors, herein we report a new quinoidal building block that terminated by indandione. By introducing Br atoms into the terminal benzene rings of indandione, two CPs, P2TbTI‐DPP and P2TbTI‐TIID, are synthesized through Stille polycondensation. The strong electron‐withdrawing ability of indandione‐terminated quinoidal unit enables P2TbTI‐DPP and P2TbTI‐TIID with low‐lying LUMO energy levels of ~‐3.90 eV. Organic thin‐film transistors based on P2TbTI‐DPP and P2TbTI‐TIID exhibit n‐type transport behavior. Besides, it is found that the electron mobility of these two polymers is weakly dependent on the annealing temperature due to the near‐amorphous of polymer thin‐film.This article is protected by copyright. All rights reserved

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Redox Polymers: Opportunities and Challenges in their Unique Functionalities

Nishide

2024

Macro Chemistry & Physics

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The growing demand for energy‐storage devices has raised inevitable concerns regarding the availability of redox‐active inorganic compounds and metals. It is expected that some of the inorganic compounds will be replaced by organic redox polymers, which are produced from abundant sources using environmentally benign processes, and they exhibit inherent advantages, including flexibility, processability, and biocompatibility. Redox polymers contain groups that can be reversibly reduced and oxidized by gaining and releasing electrons, respectively, and constitute an emerging class of functional organic materials. This article begins with a retrospective discussion of polymers and their electron exchange concepts, presenting them as old but new materials. The basics of electrochemical redox couples are briefly reintroduced, and the chemical design strategies for extending them to redox polymers are summarized. Subsequently, the efficient and reversible charge propagation and storage in densely populated redox‐active sites on soft polymer platforms are discussed. The potential to employ redox polymers in rechargeable charge‐storage applications and next‐generation devices is discussed, along with the current challenges and prospects. This outlook suggests fundamental questions and proposes interesting topics for redox polymers to facilitate their development as valuable materials for use in sustainable technologies.

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Biosourced Monomers: Toward Sustainable Conjugated Polymers for Organic Electronics

Cited by 10 publications

References 113 publications

Degradable π-Conjugated Polymers

Degradable π-Conjugated Polymers

Synthesis and Characterization of Conjugated Polymers Based on Thieno[3,4‐b]Thiophene Quinoidal Unit

Redox Polymers: Opportunities and Challenges in their Unique Functionalities

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