Conjugated molecules for colourimetric and fluorimetric sensing of sodium and potassium

Parr, Zachary S.; Nielsen, Christian B.

doi:10.1039/d0qm00157k

Cited by 10 publications

(6 citation statements)

References 36 publications

(40 reference statements)

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“…Dual fluoroand chromoionophores have also been synthesized according to a similar method with both M−Na + and M−K + . 168 The authors demonstrated both ratiometric and fluorimetric sensing of both Na + and K + alongside the well-reported ionochromic response. Utilizing the tunability of the optoelectronic properties of conjugated materials, the authors demonstrate a bimolecular Na + /K + sensing system with a discrete colorimetric response to Na + or K + or both in solution.…”

Section: Ion-selective Interactionsmentioning

confidence: 99%

“…The molecules exhibit a low limit of detection across the visible spectrum. Dual fluoro- and chromoionophores have also been synthesized according to a similar method with both M–Na + and M–K + . The authors demonstrated both ratiometric and fluorimetric sensing of both Na + and K + alongside the well-reported ionochromic response.…”

Section: Ionic Interactions In Small-molecule Semiconductorsmentioning

confidence: 99%

Section: Ionic Interactions In Small-molecule Semiconductorsmentioning

confidence: 99%

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Mixed Ionic and Electronic Conduction in Small-Molecule Semiconductors

et al. 2021

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Small-molecule organic semiconductors have displayed remarkable electronic properties with a multitude of π-conjugated structures developed and fine-tuned over recent years to afford highly efficient hole- and electron-transporting materials. Already making a significant impact on organic electronic applications including organic field-effect transistors and solar cells, this class of materials is also now naturally being considered for the emerging field of organic bioelectronics. In efforts aimed at identifying and developing (semi)conducting materials for bioelectronic applications, particular attention has been placed on materials displaying mixed ionic and electronic conduction to interface efficiently with the inherently ionic biological world. Such mixed conductors are conveniently evaluated using an organic electrochemical transistor, which further presents itself as an ideal bioelectronic device for transducing biological signals into electrical signals. Here, we review recent literature relevant for the design of small-molecule mixed ionic and electronic conductors. We assess important classes of p- and n-type small-molecule semiconductors, consider structural modifications relevant for mixed conduction and for specific interactions with ionic species, and discuss the outlook of small-molecule semiconductors in the context of organic bioelectronics.

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Section: Ion-selective Interactionsmentioning

confidence: 99%

Section: Ionic Interactions In Small-molecule Semiconductorsmentioning

confidence: 99%

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Mixed Ionic and Electronic Conduction in Small-Molecule Semiconductors

et al. 2021

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“…40,41 When translated to a crown ether, analyte specificity may also be introduced; incorporation of 15-crown-5, a well-known sodium-chelating group, can impart the capacity for a selective sensing response to Na + , as previously recorded in analogous materials. 36,42,43 Synthetic route was also considered, and the Staudinger-Vilarrasa reaction 44 was selected as a suitable method, based on its prior success modifying EDOT to make electropolymerizable monomers in good yield 30 and the corresponding formation of an amide: a rigid and polar group which may aid adhesion to ITO, as has been demonstrated with other hydrogen-bonding carbonyl groups. 18…”

Section: Monomer Designmentioning

confidence: 99%

Controlling morphology, adhesion, and electrochromic behavior of PEDOT films through molecular design and processing

Kousseff

Taifakou

Neal

et al. 2021

Journal of Polymer Science

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Poly(3,4-ethylenedioxythiophene) (PEDOT) is a well-known semiconducting polymer with favorable properties which find it often applied as the active material in biological sensors and electrochromic devices. However, PEDOT has several drawbacks which can prohibit its effective or long-term use, including weak adhesion to substrates such as ITO-coated glass, poorly controlled surface morphology, and reduced electrochemical stability over time. While a diverse range of approaches have been explored to overcome these issues, most involve additives or substrate modification, while solutions based on direct covalent adaptation are relatively lacking. We present a novel polymer based on covalently modified EDOT (PEDOT-Crown), featuring polar motifs and a 15-crown-5 moiety. Compared to PEDOT, PEDOT-Crown demonstrates a wealth of advantageous properties including: superior adhesion to ITO under physical and electrochemical duress; a more uniform surface morphology; and electrochemical properties including a higher contrast ratio, red-shifted polaron and bipolaron absorption features, bleaching of the neutral absorption band across a narrower voltage range, and more Faradaic rather than capacitive behavior. Additionally, we note that in the presence of Na + , PEDOT-Crown appears to show modified behavior in long-term electrochemical experiments. These features make PEDOT-Crown a material with improved suitability for application in biological sensing and electrochromic devices, compared to PEDOT.

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“…Researcher devoted more efforts for the recognition of sodium (Na + ) using crown ethers motif such as SBFI (sodium‐binding benzofuran isophthalate), [15] sodium green, [16] two photon excited probe, [17–19] crown ether‐appended boron dipyrrin, [20] ratiometric optical probes, [21,22] PET based optical probes, [23–25] calix[4] arene derivative bearing pyrene and perylene, [26] squaraine compound [27] sensors based on enzymes [28] . Several fluorescent based probes have been developed for sodium ions [29–31] . However, they were based on crown ether derived chelators, peptides, enzymes, proteins, and nucleic acids.…”

Section: Introductionmentioning

confidence: 99%

Small‐Molecule Fluorescent Probe: Ratiometric and Selective Detection of Sodium Ions for Imaging and Solid‐State Sensing Applications

Shankar¹,

Aravind

Ashokkumar

et al. 2022

ChemistrySelect

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A ratiometric highly fluorescent small molecular probe (L), 1,2,4-triazol-4-yliminomethyl-5-(hydroxymethyl)-2-methylpyridin-3-ol, was designed for detecting Na(I) ions in DMF:water (1 : 9, v/v) medium. The chemical structure of Na(I) complex of probe was confirmed by single crystal XRD. The fluorescence detection of Na + ion has been executed in both solid and solution medium. The observations suggest the same chemical structure in solution state as well. The detailed photochemical studies showed that highly selective sensing of Na + ions even in the presence of common interfering K + ions. The fluorescence decay studies showed that the lifetime of NaL is lesser than L. The excited state intramolecular proton transfer (ESIPT) mechanism and the nature of electronic transitions were examined by quantum chemical studies. The electrochemical behaviour was studied by cyclic voltammetry and impedance spectra. It has also been shown that the probe can be applied to paper based sensing and imaging of Na + ions in U87 cell lines.

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Conjugated molecules for colourimetric and fluorimetric sensing of sodium and potassium

Abstract: New alkali metal ion sensors showing ratiometric colourimetric and fluorimetric responses with high selectivity and low limits of detection.

Cited by 10 publications

References 36 publications

Mixed Ionic and Electronic Conduction in Small-Molecule Semiconductors

Mixed Ionic and Electronic Conduction in Small-Molecule Semiconductors

Controlling morphology, adhesion, and electrochromic behavior of PEDOT films through molecular design and processing

Small‐Molecule Fluorescent Probe: Ratiometric and Selective Detection of Sodium Ions for Imaging and Solid‐State Sensing Applications

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