Thiol–Ene Click Post-Polymerization Modification of a Fluorescent Conjugated Polymer for Parts-per-Billion Pyrophosphate Detection in Seawater

Williams, Abagail K.; Tropp, Joshua; Crater, Erin R.; Eedugurala, Naresh; Azoulay, Jason D.

doi:10.1021/acsapm.8b00064

Cited by 21 publications

(8 citation statements)

References 30 publications

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“…The reported synthetic strategy is highly tunable, as a variety of monomers bearing other chemistries for postmodification can be utilized to generate conjugated polymers and polyelectrolytes for bioelectronic applications. 20,42,51 These results build upon the growing literature of designing conductive polymers for biomaterial incorporation and lay the groundwork for an extension of PEDOT-NHS copolymers into regenerative engineering, sensing, and other bioelectronic applications.…”

Section: Discussionmentioning

confidence: 64%

“…With increased loading of EDOT-NHS, the shift at 1517 cm -1 was relatively stronger in PEDOT-NHS 50 which may be attributed to elevated N-H bending from the secondary amide which attaches the NHS side chain overlapping with the C=C stretching from the polymer backbone. Characteristic S=O stretching vibrations were also observed from thee sulfonate salts at 1038 cm -1 42. Elemental analysis of both materials was performed to determine the amount of EDOT-NHS incorporation within each polymer.…”

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confidence: 99%

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PEDOT-NHS as a Versatile Conjugated Polyelectrolyte for Bioelectronics

Tropp¹,

Mehta²,

Wu³

et al. 2022

Preprint

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The field of bioelectronics leverages the optoelectronic properties of synthetic materials to interface with living systems. These applications require materials that are conductive, aqueous processible, biocompatible, and can be chemically modified for biofunctionalization. While conjugated polymers and polyelectrolytes have been reported that demonstrate several of these features, materials that offer each of these properties simultaneously are rare. Here, we developed copolymers of anionic polyelectrolyte poly(4-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-butane-1-sulfonic acid sodium salt (PEDOT-S), containing structural units with amine-reactive NHS-esters. The reported PEDOT-NHS copolymers demonstrate water-solubility and electrical conductivities similar to previously reported PEDOT-S, as well as the ability to bind important amine-rich biomaterials. Furthermore, the PEDOT-NHS copolymers were biocompatible and hemocompatible, and therefore show promise for next-generation bioelectronic and regenerative engineering applications.

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Section: Discussionmentioning

confidence: 64%

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confidence: 99%

PEDOT-NHS as a Versatile Conjugated Polyelectrolyte for Bioelectronics

Tropp¹,

Mehta²,

Wu³

et al. 2022

Preprint

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“…[ 17 ] Unlike small‐molecule systems, CPs transduce signals through excited state (exciton) migration, which is relatively immune to electrostatic and dielectric variations, allowing their successful implementation in complex aqueous environments. [ 16c,17a,18 ]…”

Section: Introductionmentioning

confidence: 99%

A Sensor Array for the Ultrasensitive Discrimination of Heavy Metal Pollutants in Seawater

Ihde

Tropp

Díaz

et al. 2022

Adv Funct Materials

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Metal cations are potent environmental pollutants that negatively impact human health and the environment. Despite advancements in sensor design, the simultaneous detection and discrimination of multiple heavy metals at sub‐nanomolar concentrations in complex analytical matrices remain a major technological challenge. Here, the design, synthesis, and analytical performance of three highly emissive conjugated polyelectrolytes (CPEs) functionalized with strong iminodiacetate and iminodipropionate metal chelates that operate in challenging environmental samples such as seawater are demonstrated. When coupled with array‐based sensing methods, these polymeric sensors discriminate among nine divalent metal cations (CuII, CoII, NiII, MnII, FeII, ZnII, CdII, HgII, and PbII). The unusually high and robust luminescence of these CPEs enables unprecedented sensitivity at picomolar concentrations in water. Unlike previous array‐based sensors for heavy metals using CPEs, the incorporation of distinct π‐spacer units within the polymer backbone affords more pronounced differences in each polymer's spectroscopic behavior upon interaction with each metal, ultimately producing better analytical information and improved differentiation. To demonstrate the environmental and biological utility, a simple two‐component sensing array is showcased that can differentiate nine metal cation species down to 500 × 10−12 m in aqueous media and to 100 × 10−9 m in seawater samples collected from the Gulf of Mexico.

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“…polybutadiene 42 ) can be decorated with a broad variety of functionalities to obtain innovative macromolecules with tailor-made properties. Among the different reactions enabling PPMs (copper-catalyzed azidealkyne cycloaddition (CuAAC), 43 thiol-ene addition, 44 Michael addition, 45 or electrophilic cascade reactions 42 ), active esters, such as pentafluorophenyl (PFP) esters, [46][47][48] are considerably attractive functional units to deliver well-defined multi-functionalized polymers. Especially the possibility to modify active PFP ester groups within a copolymer backbone in a precise and orthogonal manner is highly beneficial.…”

Section: Introductionmentioning

confidence: 99%