Protonic acid doping of low band-gap conjugated polyions

Ye, Gang; Liu, Yuru; Liu, Jian; Qiu, Xinkai; Koster, L. Jan Anton; Chiechi, Ryan C.

doi:10.1039/d0qm00278j

Cited by 3 publications

(1 citation statement)

References 35 publications

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“…To rationalize the solvent dependence of the polymers’ degradation, we examined the UV–vis spectra of pDPP(C4)-TIT across all three solutions right after adding equivalent amounts of TFA and water (Figure f and Figure S33). A redshift in the absorption spectra was observed for all polymer solutions upon addition of acid due to potential acid doping, − with the largest redshift seen in chlorobenzene solution. We hypothesize that the redshift corresponded to acid-induced aggregation, which resulted in the slowest degradation for polymers in chlorobenzene solution.…”

Section: Resultsmentioning

confidence: 93%

Impact of Molecular Design on Degradation Lifetimes of Degradable Imine-Based Semiconducting Polymers

et al. 2022

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Transient electronics are a rapidly emerging field due to their potential applications in the environment and human health. Recently, a few studies have incorporated acid-labile imine bonds into polymer semiconductors to impart transience; however, understanding of the structure−degradation property relationships of these polymers is limited. In this study, we systematically design and characterize a series of fully degradable diketopyrrolopyrrole-based polymers with engineered sidechains to investigate the impact of several molecular design parameters on the degradation lifetimes of these polymers. By monitoring degradation kinetics via ultraviolet−visible spectroscopy, we reveal that polymer degradation in solution is aggregationdependent based on the branching point and M n , with accelerated degradation rates facilitated by decreasing aggregation. Additionally, increasing the hydrophilicity of the polymers promotes water diffusion and therefore acid hydrolysis of the imine bonds along the polymer backbone. The aggregation properties and degradation lifetimes of these polymers rely heavily on solvent, with polymers in chlorobenzene taking six times as long to degrade as in chloroform. We develop a new method for quantifying the degradation of polymers in the thin film and observe that similar factors and considerations (e.g., interchain order, crystallite size, and hydrophilicity) used for designing high-performance semiconductors impact the degradation of imine-based polymer semiconductors. We found that terpolymerization serves as an attractive approach for achieving degradable semiconductors with both good charge transport and tuned degradation properties. This study provides crucial principles for the molecular design of degradable semiconducting polymers, and we anticipate that these findings will expedite progress toward transient electronics with controlled lifetimes.

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Section: Resultsmentioning

confidence: 93%

Impact of Molecular Design on Degradation Lifetimes of Degradable Imine-Based Semiconducting Polymers

et al. 2022

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Self‐Doping and Self‐Acid‐Doping of Conjugated Polymer Bioelectronics: The Case for Accuracy in Nomenclature

Fidanovski,

Gu,

Travaglini

et al. 2023

Adv Healthcare Materials

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Conjugated polymers are enabling the development of flexible bioelectronics, largely driven by their organic nature which facilitates modification and tuning to suit a variety of applications. As organic semiconductors, conjugated polymers require a dopant to exhibit electrical conductivity, which in physiological conditions can result in dopant loss and thereby deterioration in electronic properties. To overcome this challenge, “self‐doped” and self‐acid‐doped conjugated polymers having ionised pendant groups covalently bound to their backbone are being developed. The ionised group in a “self‐doped” polymer behaves as the counterion that mainatins electroneutrality, while an external dopant is required to induce charge transfer. The ionised group in a self‐acid‐doped polymer induces charge transfer and behaves as the counterion balancing the charges. Despite their doping processes being different, the two terms, self‐doped and self‐acid‐doped, are often used interchangeably in the literature. This review highlights the differences in the doping mechanisms of self‐doped and self‐acid‐doped polymers, and proposes that the term “self‐doped” should be replaced by “self‐compensated”, while reserving the term self‐acid‐doped for polymers that are intrinsically doped without the need of an external dopant. This is followed by a summary of examples of self‐acid‐doping in bioelectronics, highlighting their stability in the conductive state under physiological conditions.This article is protected by copyright. All rights reserved

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The relationships between surface and electrical properties of CSA doped PANI films

Özbay

Korkut

Erden

2023

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Protonic acid doping of low band-gap conjugated polyions

Abstract: Conjugated polyions (CPIs) offer synthetic tunability and selective processing into insulating, semiconducting and metallic states simply by controlling acidity.

Cited by 3 publications

References 35 publications

Impact of Molecular Design on Degradation Lifetimes of Degradable Imine-Based Semiconducting Polymers

Impact of Molecular Design on Degradation Lifetimes of Degradable Imine-Based Semiconducting Polymers

Self‐Doping and Self‐Acid‐Doping of Conjugated Polymer Bioelectronics: The Case for Accuracy in Nomenclature

The relationships between surface and electrical properties of CSA doped PANI films

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