Nuclear Magnetic Resonance Spectroscopy Investigations of Naphthalene-Based 1,2,3-Triazole Systems for Anion Sensing

Aiken, Karelle; Bunn, Jessica; Sutton, S. R.; Christianson, Matthew; Winder, Domonique; Freeman, C. Daniel; Padgett, Clifford W.; McMillen, Colin D.; Ghosh, Dipak; Landge, Shainaz M.

doi:10.3390/magnetochemistry4010015

Cited by 11 publications

(4 citation statements)

References 75 publications

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“…Eventually, the resonances of H-8, H-6, and H-4 broadened out into the baseline of the spectra. Consistent with the behavior of PTP and similar molecules [14,21,24,25], these changes in the H-8 and phenol group's chemical shifts indicated coordination between P01′s −OH unit and F − (Scheme 2 and Figure 2). Thus, the non-fluorometric response of P01 was solely due to the quenching effect of the nitro group [29][30][31].…”

Section: Response With Synthetic Precursorssupporting

confidence: 72%

“…For all polymeric chemosensor syntheses, azobisisobutyronitrile (AIBN) was used as the free radical initiator. To match the concentration of chemosensor used in previous studies in solution [21,24,25], P04, P05, P06, and P07 were prepared with a P03 concentration of 0.1 mol%. Additionally, another two styrene-based chemosensors were synthesized with P03 concentrations of 1.0 mol% and 10.0 mol% .…”

Section: Synthesis Of Polymeric Chemosensors: P04 P05 P06 and P07mentioning

confidence: 99%

“…In all cases, AIBN was used as the initiator for bulk free-radical polymerization. The polymeric sensors prepared with acrylic acid, methyl methacrylate, and divinylbenzene were made with a P03 concentration of 0.1 mol% to mimic the solution concentration of PTP used in earlier sensing studies [21,24,25]. This allowed for a comparative analysis between earlier data and the immobilized sensors described here.…”

Section: Synthesis Of Polymersmentioning

confidence: 99%

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Exploring the Effects of Various Polymeric Backbones on the Performance of a Hydroxyaromatic 1,2,3-Triazole Anion Sensor

Ugboya

Monroe

Ofulue

et al. 2020

Sensors

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Polymeric chemosensors are vital sensing tools because of higher sensitivity compared to their monomeric counterparts and tunable mechanical properties. This study focuses on the incorporation of a hydroxyaromatic 1,2,3-triazole sensor, 2-(4-phenyl 1H-1,2,3-triazol-1-yl)phenol (PTP), into polymers. By itself, the triazole has a selective, fluorometric response to the fluoride, acetate, and dihydrogen phosphate anions, and is most responsive to fluoride. Current investigations probe the suitability of various polymeric backbones for the retention and enhancement of the triazole’s sensing capabilities. Backbones derived from acrylic acid, methyl methacrylate, divinylbenzene, and styrene were explored. UV-illumination, Nuclear Magnetic Resonance (NMR) titration, and ultraviolet-visible (UV-Vis) absorption and fluorescence spectroscopy studies are used to investigate the performance of newly synthesized polymers and the derivatives of PTP that serve as the polymers’ precursors. Among the polymers investigated, copolymers with styrene proved best; these systems retained the sensing capabilities and were amenable to tuning for sensitivity.

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Section: Response With Synthetic Precursorssupporting

confidence: 72%

Section: Synthesis Of Polymeric Chemosensors: P04 P05 P06 and P07mentioning

confidence: 99%

Section: Synthesis Of Polymersmentioning

confidence: 99%

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Exploring the Effects of Various Polymeric Backbones on the Performance of a Hydroxyaromatic 1,2,3-Triazole Anion Sensor

Ugboya

Monroe

Ofulue

et al. 2020

Sensors

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“…In this study, we will exploit the recognition capabilities of the 1,2,3-triazole chemosensors [ 13 ] in logic applications to access real-time diagnostic and memory devices [ 14 ]. The triazole derivatives synthesized by our group are known for sensing and reversible characteristics [ 15 , 16 , 17 , 18 , 19 , 20 ]. We realized that logic functions can be aptly used to access applications such as real-time diagnostics, molecular devices, and therapeutics [ 14 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

1,2,3-Triazoles: Controlled Switches in Logic Gate Applications

Ghosh,

Atkinson,

Gibson

et al. 2023

Sensors

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A 1,2,3-triazole-based chemosensor is used for selective switching in logic gate operations through colorimetric and fluorometric response mechanisms. The molecular probe synthesized via “click chemistry” resulted in a non-fluorescent 1,4-diaryl-1,2,3-triazole with a phenol moiety (PTP). However, upon sensing fluoride, it TURNS ON the molecule’s fluorescence. The TURN-OFF order occurs through fluorescence quenching of the sensor when metal ions, e.g., Cu2+, and Zn2+, are added to the PTP-fluoride ensemble. A detailed characterization using Nuclear Magnetic Resonance (NMR) spectroscopy in a sequential titration study substantiated the photophysical characteristics of PTP through UV-Vis absorption and fluorescence profiles. A combination of fluorescence OFF-ON-OFF sequences provides evidence of 1,2,3-triazoles being controlled switches applicable to multimodal logic operations. The “INH” gate was constructed based on the fluorescence output of PTP when the inputs are F− and Zn2+. The “IMP” and “OR” gates were created on the colorimetric output responses using the probe’s absorption with multiple inputs (F− and Zn2+ or Cu2+). The PTP sensor is the best example of the “Write-Read-Erase-Read” mimic.

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The influence of amino substituents on the signal‐output, selectivity, and sensitivity of a hydroxyaromatic 1,2,3‐triazolyl chemosensor for anions—A structure–property relationship investigation

Ghosh

Landge

Zhu

et al. 2020

J of Physical Organic Chem

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The influence of strongly electron donating amino groups on a hydroxyaromatic 1,2,3‐triazolyl anion chemosensor was investigated with spectroscopic studies (ultraviolet‐visible [UV‐vis], fluorescence, and nuclear magnetic resonance [NMR]) and computational analyses. This work focused on 2‐, 3‐ and 4‐amino derivatives of the parent molecule, 2‐(4‐phenyl‐1H‐1,2,3‐triazol‐1‐yl)phenol (PTP). The effect on signal‐output, selectivity, sensitivity, and the mechanism of response was explored. In all cases, the incorporation of the amino group enhances fluorescence during anion detection while retaining key properties (the receptor site, a blue‐fluorescent response, and the ability to detect F−, H2PO4−, and AcO−—strongest response to F−). Specifically, sensitivity to F− is impacted by the amino group's location. The 2‐amino is most responsive to F−, more than PTP and the other amino regioisomers. Results from this work are important for developing predictive, structure‐signal tuning models, which will be used in the targeted design of sensors based on the PTP scaffold.

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Nuclear Magnetic Resonance Spectroscopy Investigations of Naphthalene-Based 1,2,3-Triazole Systems for Anion Sensing

Cited by 11 publications

References 75 publications

Exploring the Effects of Various Polymeric Backbones on the Performance of a Hydroxyaromatic 1,2,3-Triazole Anion Sensor

Exploring the Effects of Various Polymeric Backbones on the Performance of a Hydroxyaromatic 1,2,3-Triazole Anion Sensor

1,2,3-Triazoles: Controlled Switches in Logic Gate Applications

The influence of amino substituents on the signal‐output, selectivity, and sensitivity of a hydroxyaromatic 1,2,3‐triazolyl chemosensor for anions—A structure–property relationship investigation

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