Highly fluorescent purine-containing conjugated copolymers with tailored optoelectronic properties

O’Connell, Caela; Sabury, Sina; Jenkins, Justin; Collier, Graham S.; Sumpter, Bobby G.; Long, Brian K.; Kilbey, S. Michael

doi:10.1039/d2py00545j

Cited by 5 publications

(7 citation statements)

References 82 publications

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“…[ 58 ] Purine‐containing copolymers have also demonstrated that 9–12 rings was sufficient to obtain the ECL. [ 59 ] As it pertains to these azomethine‐containing DHPPs, each repeat unit of 3B contains four aromatic rings—three benzene rings and a fused pyrrolopyrrole—meaning each polymer chain would have an average of ≈20 rings, since the degree of polymerization was calculated to be ≈5. Even though the M n of 3B is relatively low, 20 rings is believed meet the threshold for ECL where the measured optical properties are assumed to be an accurate representation for the polymer.…”

Section: Resultsmentioning

confidence: 99%

Azomethine‐Containing Pyrrolo[3,2‐b]pyrrole Copolymers for Simple and Degradable Conjugated Polymers

Bartlett,

Charland‐Martin,

Lawton

et al. 2023

Macromol. Rapid Commun.

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Conjugated polymers have received significant attention as potentially lightweight and highly tailorable alternatives to inorganic semiconductors, but their synthesis is often complex, produces toxic byproducts, and they are not typically designed to be degradable or recyclable. These drawbacks necessitate dedicated efforts to discover materials with design motifs that enable targeted and efficient degradation of conjugated polymers. In this vein, the synthetic simplicity of 1,4‐dihydropyrrolo[3,2‐b]pyrroles (DHPPs) is exploited to access azomethine‐containing copolymers via a benign acid‐catalyzed polycondensation protocol. Polymerizations involve reacting a dialdehyde‐functionalized dihydropyrrolopyrrole with p‐phenylenediamine as the comonomer using p‐toluenesulfonic acid as a catalyst. The inherent dynamic equilibrium of the azomethine bonds subsequently enabled the degradation of the polymers in solution in the presence of acid. Degradation of the polymers is monitored via NMR, UV‐vis absorbance, and fluorescence spectroscopies, and the polymers are shown to be fully degradable. Notably, while absorbance measurements reveal a continued shift to higher energies with extended exposure to acid, fluorescence measurements show a substantial increase in the fluorescence response upon degradation. Results from this study encourage the continued development of environmentally‐conscious polymerizations to attain polymeric materials with useful properties while simultaneously creating polymers with structural handles for end‐of‐life management or/and recyclability.

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Section: Resultsmentioning

confidence: 99%

Azomethine‐Containing Pyrrolo[3,2‐b]pyrrole Copolymers for Simple and Degradable Conjugated Polymers

Bartlett,

Charland‐Martin,

Lawton

et al. 2023

Macromol. Rapid Commun.

Self Cite

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“…Compared to homopolymers, copolymers are special CPs with excellent optical luminescent and electrical conducting properties due to their extensive π-conjugation [ 30 ]. Moreover, copolymers also possess some advantages in development of advanced biosensor devices such as tailorable structures, tunable optoelectronic properties, processability, high solubility and stability, and ease of device fabrication [ 31 ]. The properties of common homo- and co-CPs used for preparation and design of biosensors are summarized in Table 2 .…”

Section: Structures and Characteristics Of Conjugated Polymers For Bi...mentioning

confidence: 99%

Recent Advances in Conjugated Polymer-Based Biosensors for Virus Detection

2023

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Nowadays, virus pandemics have become a major burden seriously affecting human health and social and economic development. Thus, the design and fabrication of effective and low-cost techniques for early and accurate virus detection have been given priority for prevention and control of such pandemics. Biosensors and bioelectronic devices have been demonstrated as promising technology to resolve the major drawbacks and problems of the current detection methods. Discovering and applying advanced materials have offered opportunities to develop and commercialize biosensor devices for effectively controlling pandemics. Along with various well-known materials such as gold and silver nanoparticles, carbon-based materials, metal oxide-based materials, and graphene, conjugated polymer (CPs) have become one of the most promising candidates for preparation and construction of excellent biosensors with high sensitivity and specificity to different virus analytes owing to their unique π orbital structure and chain conformation alterations, solution processability, and flexibility. Therefore, CP-based biosensors have been regarded as innovative technologies attracting great interest from the community for early diagnosis of COVID-19 as well as other virus pandemics. For providing precious scientific evidence of CP-based biosensor technologies in virus detection, this review aims to give a critical overview of the recent research related to use of CPs in fabrication of virus biosensors. We emphasize structures and interesting characteristics of different CPs and discuss the state-of-the-art applications of CP-based biosensors as well. In addition, different types of biosensors such as optical biosensors, organic thin film transistors (OTFT), and conjugated polymer hydrogels (CPHs) based on CPs are also summarized and presented.

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“…These polymers were highly fluorescent with photoluminescence quantum yields as high as ϕ = 0.61. [115] On the other hand, pyrimidines have seen more uses in conjugated polymers. In 2013, Gunathilake et al made a series of pyrimidine-based conjugated polymers (Scheme 10) by aldol condensation reaction.…”

Section: Pyrimidine and Purinesmentioning

confidence: 99%

“…𝜋-conjugated materials obtained by O'Connell's et al incorporating purine in the main chain. [115] Scheme 10. 𝜋-conjugated polymers incorporating pyrimidine in the main chain obtained by Gunathilake et al [116] It is not to say that biocatalysis is without any problems, yields tend to be low. Although there is room for development with all the tools to genetically modify organisms, according to researchers in the field, this kind of optimization [117] Scheme 11.…”

Section: Indigoidinementioning

confidence: 99%

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Biosourced Monomers: Toward Sustainable Conjugated Polymers for Organic Electronics

Boivin

Dupont

Gendron

et al. 2022

Macro Chemistry & Physics

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Organic electronic materials are starting to appear in various applications, but there are still hurdles to overcome before the average consumer can get them in their hands. Right now, most polymers in the field of organic electronics are made from petroleum derivatives. However, new sources of platform chemicals and monomers are being explored. This perspective article highlights ways that have been explored to avoid the use of petrochemicals and demonstrates new pathways that can be taken to increase the sustainability of conjugated polymers in organic electronics.

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Highly fluorescent purine-containing conjugated copolymers with tailored optoelectronic properties

Abstract: Conjugated copolymers containing electron donor and acceptor units in their main chain have emerged as promising materials for organic electronic devices due to their tunable optoelectronic properties.

Cited by 5 publications

References 82 publications

Azomethine‐Containing Pyrrolo[3,2‐b]pyrrole Copolymers for Simple and Degradable Conjugated Polymers

Azomethine‐Containing Pyrrolo[3,2‐b]pyrrole Copolymers for Simple and Degradable Conjugated Polymers

Recent Advances in Conjugated Polymer-Based Biosensors for Virus Detection

Biosourced Monomers: Toward Sustainable Conjugated Polymers for Organic Electronics

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