Quinolizinium-based fluorescent probes for formaldehyde detection in aqueous solution, serum, and test strip <i>via</i> 2-aza-Cope rearrangement

Tantipanjaporn, Ajcharapan; Kung, Karen Ka‐Yan; Sit, Hoi-Yi; Wong, Man Leung

doi:10.1039/d2ra01397e

Cited by 14 publications

(5 citation statements)

References 24 publications

(30 reference statements)

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“…The mechanism proceeds through an intermediate chairlike structure. The rearrangement shifts single and double bonds between two allylic parts . In this case, sigmatropic rearrangements are involved in pericyclic reactions, where the σ bond in the adjacency of pi systems is transferred and the overall pi system reestablishes itself (Figure ).…”

Section: Organic Chemosensorsmentioning

confidence: 99%

“…The rearrangement shifts single and double bonds between two allylic parts. 25 In this case, sigmatropic rearrangements are involved in pericyclic reactions, where the σ bond in the adjacency of pi systems is transferred and the overall pi system reestablishes itself ( Figure 3 ). The total number of sigma and pi bonds is preserved in the end.…”

Section: Organic Chemosensorsmentioning

confidence: 99%

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Recent Progress in the Development of Organic Chemosensors for Formaldehyde Detection

et al. 2023

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Formaldehyde has become a prominent topic of interest because of its simple molecular structure, release from various compounds in the near vicinity of humans, and associated hazards. Thus, several researchers designed sophisticated instrumentations for formaldehyde detection that exhibit real-time sensing properties and are cost-effective and portable with high detection limits. On these grounds, this review is centered on an analysis of optical chemosensors for formaldehyde that specifically fall under the broad spectrum of organic probes. In this case, this review discusses different organic functionalities, including amines, imines, aromatic pillar arenes, β-ketoesters, and β-diketones, taking part in various reaction mechanisms ranging from aza-Cope rearrangement and Schiff base and Hanztch reactions to aldimine condensation. In addition, this review distinguishes reaction mechanisms according to photophysical phenomena, that is, aggregation-induced emission, photoinduced electron transfer, and intramolecular charge transfer. Furthermore, it addresses the instrumentation involved in gas-based and liquid formaldehyde detection. Finally, it discusses the gaps in existing technologies followed by a succinct set of recommendations for future research.

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Section: Organic Chemosensorsmentioning

confidence: 99%

Section: Organic Chemosensorsmentioning

confidence: 99%

Recent Progress in the Development of Organic Chemosensors for Formaldehyde Detection

et al. 2023

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“…Though governments explicitly prohibit the addition of excessive amounts of FA to household products, it is still detected in cosmetic products, fruit transportation, fish preservation, etc for preventing spoilage due to the ability to effectively inhibit the survival of most bacteria and fungi in water [4][5][6]. For efficient and simple field detection, electrochemical sensors have been utilized for FA detection instead of spectrophotometry, high-performance liquid chromatography, gas chromatography, fluorometric methods, polarography, etc [7][8][9][10][11][12]. Finding an efficient electrode material for an electrochemical sensor, so that it has a fast response performance to FA, is the key to the current breakthrough in FA electrochemical detection technology [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Efficient formaldehyde sensor based on PtPd nanoparticles-loaded nafion-modified electrodes

Xu,

Jiang,

Huang

et al. 2023

Nanotechnology

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The noble metal-based electrochemical sensor design for efficient and stable formaldehyde(FA) detection is important ongoing research. In this paper, PtPd/Nafion/GCE is prepared by electrochemical cyclic voltammetry (CV) deposition method based on electrodepositing nanostructured platinum (Pt)-palladium (Pd) nanoparticles in Nafion film-coated glassy carbon electrode (GCE). The influence of deposition parameters and chemical composition (atomic ratio of Pt and Pd) on the electrochemical behaviour of PtPd/Nafion/GCE has been investigated. PtPd/Nafion/GCE displays a remarked electrocatalytic activity for the oxidation of FA and exhibits a linear relationship in the range of 10 to 5000 μM, with a detection limit of 3.3 μM in 0.1 M H2SO4 solution. It is proved that the detection performance of PtPd/Nafion/GCE electrode is valuable for further application with low detection limit, wide linear range, favourable selectivity and high response.

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“…[11d,12n,13-16] It has been also recently shown that compounds possessing the quinolizinium moiety with extended π-conjugated systems can be prepared on Au surface from the parental pyridinium salt via cyclodehydrogenation reactions. [17] As far as potential application of compounds with the quinolizinium moiety is concerned, they have so far found application as DNA intercalators, [18] photosensitizers in biological systems, [19] photosensitizers in biological systems, [13,14] probes for detection of small molecules, [20] photocatalysts, [21] or non-linear optical chromophores. [22] One class of the above-mentioned Ne-PAHs are N-embedded pyrene derivatives (Figure 1), i. e. azapyrenes that could be considered as suitable and interesting model substances or intermediates en route to NeNs.…”

Section: Introductionmentioning

confidence: 99%

“…As far as potential application of compounds with the quinolizinium moiety is concerned, they have so far found application as DNA intercalators, [18] photosensitizers in biological systems, [19] photosensitizers in biological systems, [13,14] probes for detection of small molecules, [20] photocatalysts, [21] or non‐linear optical chromophores [22] …”

Section: Introductionmentioning

confidence: 99%

Catalytic C−C/C−H Bond Activation Relay for Synthesis of Fluorescent Naphthoquinolizinium Salts

et al. 2023

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Herein, we report the design and synthesis of a series of novel cationic nitrogen‐embedded polyaromatic hydrocarbons with a planar geometry. The synthetic pathway is based on catalytic C−C/C−H bond activation relay that enabled preparation of regioselectively 5,6,10,11‐tetrasubstituted naphtho[2,1,8‐ija]quinolizinium salts bearing various types of substituents. Single‐crystal X‐ray analyses of selected compounds confirmed planarity of the quinolizinium core. Most of the prepared compounds exhibited strong fluorescence (Φs up to >99 %) ranging from 420–600 nm depending on the substitution pattern. According to DFT calculations LUMO is always distributed over the quinolizinium framework regardless of the attached substituents, whereas delocalization of HOMO is related to the substitution pattern. Electrochemical measurements show irreversible reduction of all compounds, which is supported by the calculated location of LUMO orbitals.

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Quinolizinium-based fluorescent probes for formaldehyde detection in aqueous solution, serum, and test strip via 2-aza-Cope rearrangement

Abstract: Novel quinolizinium-based fluorescent probes were designed based on 2-aza-Cope rearrangement reaction to detect formaldehyde in aqueous solution, serum, and paper format. The use of a geminal dimethyl group allows fast response within 15 min.

Cited by 14 publications

References 24 publications

Recent Progress in the Development of Organic Chemosensors for Formaldehyde Detection

Recent Progress in the Development of Organic Chemosensors for Formaldehyde Detection

Efficient formaldehyde sensor based on PtPd nanoparticles-loaded nafion-modified electrodes

Catalytic C−C/C−H Bond Activation Relay for Synthesis of Fluorescent Naphthoquinolizinium Salts

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