A simple and effective 1,2,3-triazole based “turn-on” fluorescence sensor for the detection of anions

Ghosh, Dipak; Rhodes, Shannon; Hawkins, Karena; Winder, Domonique; Atkinson, Austin; Ming, Weihua; Padgett, Clifford W.; Orvis, Jeffrey A.; Aiken, Karelle; Landge, Shainaz M.

doi:10.1039/c4nj01411a

Cited by 55 publications

(49 citation statements)

References 105 publications

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“…At a higher concentration of approximately one equivalent, it splits again into two distinct resonances. These results are in accordance with the previously reported PTP sensor from our group [49]. The initial downfield and later upfield shifts of the H2 phenyl proton showed the impact of fluoride binding on the ring.…”

Section: Resultssupporting

confidence: 83%

“…At higher concentrations (2-4 equivalents), the doublet for HF 2 − ion at −144 ppm was clearly observed ( Figure S11) [59,60]. In comparison to the previously reported sensor, PTP [49], from our group, the 1 H-NMR studies with NpTP showed similar observations. The phenolic -OH proton was significantly affected but the aryl core (phenyl in PTP and the naphthyl in NpTP) was not.…”

Section: Resultssupporting

confidence: 71%

“…An emission spectrum of NpTP molecule was obtained upon exciting the molecule at 300 nm (around λ max absorption). The structured emission band spanning between 345 nm and 380 nm is due to the naphthalene moiety [65,66], whereas the band at 330 nm is a signature of the phenol triazole group [49]. With the addition of a series of tetrabutylammonium salts of ions, emission spectra of NpTP in presence of the ions (Figure 9) resulted in a similar spectral changes as the absorption profiles (Figure 8).…”

Section: Absorption and Fluorescence Studiessupporting

confidence: 51%

“…The above results support the fact that the triazole proton and the phenolic proton (-OH) are part of the binding pocket. The naphthyl protons H10 and H13-H18 are not influenced by fluoride binding [49]. Fluoride ion interaction with NpTP was investigated by evaluating the binding mechanism of the anion with the sensor.…”

Section: Resultsmentioning

confidence: 99%

“…In the case of NpTP, the triazole serves in three capacities: ligation, signaling, and recognition. Previous work by our group investigated the sensing properties of PTP (2-(4-phenyl-1-H-1,2,3-triazol-1-yl)phenol) [49]. This molecule exhibited a blue "turn-on" fluorescent response to fluoride (F − ), acetate (OAc − ) and dihydrogen phosphate (H2PO4 − ).…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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Detailed Nuclear Magnetic Resonance (NMR) spectroscopy investigations on a novel naphthalene-substituted 1,2,3-triazole-based fluorescence sensor provided evidence for the "turn-on" detection of anions. The one-step, facile synthesis of the sensors was implemented using the "Click chemistry" approach in good yield. When investigated for selectivity and sensitivity against a series of anions (F − , Cl − , Br − , I − , H 2 PO 4 − , ClO 4 − , OAc − , and BF 4 − ), the sensor displayed the strongest fluorometric response for the fluoride anion. NMR and fluorescence spectroscopic studies validate a 1:1 binding stoichiometry between the sensor and the fluoride anion. Single crystal X-ray diffraction evidence revealed the structure of the sensor in the solid state.

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Section: Resultssupporting

confidence: 83%

Section: Resultssupporting

confidence: 71%

Section: Absorption and Fluorescence Studiessupporting

confidence: 51%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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Ion recognition by 1,2,3‐triazole moieties synthesized via “click chemistry”

Singh

George

Singh

et al. 2022

Applied Organom Chemis

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1,2,3‐Triazole‐based ligands obtained through copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) have been exploited in vast array of research domains owing to the stitching of simpler molecules through a needle of Cu(I) catalyst. The numerous reports on ion(s) detection capabilities of synthesized 1,4‐disubstituted 1,2,3‐triazole ligands using absorption and fluorescence spectroscopy are accessible. This review enlists substituted 1,2,3‐triazole‐based sensor probes, since 2010, synthesized selectively by CuAAC, having the ability to sense either a single ion or multiple ions under specific set of conditions along with their detection limits. The review also apprehends the different techniques and sensing mechanisms involved in the detection of ions by chemosensor probes.

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1H‐1,2,3‐Triazole: From Structure to Function and Catalysis

Lauko

Kouwer

Rowan

2016

Journal of Heterocyclic Chem

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The heterocyclic family of azoles have recently become one of the most widely used members of the N‐heterocycles; the most prominent one being 1H‐1,2,3‐triazole and its derivatives. The sudden growth of interest in this structural motif was sparked by the advent of click chemistry, first described in the early 2000s. From the early days of click chemistry, when the accessibility of triazoles made them into one of the most versatile linkers, interest has slowly turned to the use of triazoles as functional building blocks. The presence of multiple N‐coordination sites and a highly polarized carbon atom allows for metal coordination and the complexation of anions by both hydrogen and halogen bonding. Exploitation of these multiple binding sites makes it possible for triazoles to be used in various functional materials, such as metallic and anionic sensors. More recently, triazoles have also shown their potential in catalytic systems, thus increasing their impact far beyond the initial purpose of click chemistry. This report gives an overview of the structure, functionalities, and use of triazoles with a focus on their use in catalytic systems.

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A simple and effective 1,2,3-triazole based “turn-on” fluorescence sensor for the detection of anions

Abstract: 1,2,3-Triazole based chemosensor is synthesized using “Click chemistry” approach. Addition of fluoride ion “turn-on” the fluorescence response of probe.

Cited by 55 publications

References 105 publications

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

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

Ion recognition by 1,2,3‐triazole moieties synthesized via “click chemistry”

1H‐1,2,3‐Triazole: From Structure to Function and Catalysis

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