Quinoline-based highly selective and sensitive fluorescent probe specific for Cd2+ detection in mixed aqueous media

Ding, Xin; Zhang, Feifei; Bai, Yinjuan; Zhao, Junxia; Xia, Chen; Ge, Man; Sun, Wei

doi:10.1016/j.tetlet.2017.08.068

Cited by 22 publications

(7 citation statements)

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“…Ding. et al only obtained 8-hydroxy-7-quinaldinecarbaldehyde, a product formylated in a different position [4]. In this study we propose the transformation of some newly formed aldehydes into sterically hindered crystalline Schiff bases.…”

Section: Introductionmentioning

confidence: 64%

“…Hydroxyquinoline-5-carbaldehyde (2a) beige 0.6 g (3.5 mmol, 10.1%)[25]; m.p. = 171.3-171.8 • C; 1 H-NMR (DMSO-d 6 ; 400.2 MHz) δ = 7.26 (d,3 J H,H = 8.0 Hz, 1H, aromatic), 7.78 (dd,3 J H,H = 8.6 Hz,4 J H,H = 4.1 Hz, 1H, aromatic), 8.17 (d,3 J H,H = 8.1 Hz, 1H, aromatic), 8.97 (dd,3 J H,H = 4.1 Hz,4 J H,H = 1.6 Hz, 1H, aromatic), 9.56 (dd,3 J H,H = 8.6 Hz,4 J H,H = 1.6 Hz, 1H, aromatic), 10.14 (s, 1H, HC=O);13 C{ 1 H}-NMR (DMSO-d 6 ; 100.6 MHz) δ = 110.8, 122.4, 124.6, 126.8, 133.0, 138.0, 140.2, 149.0, 159.6, 192.2; GC-MS: t r = 6.024 min, (EI) m/z (rel. int.)…”

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confidence: 99%

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Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

et al. 2020

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A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements.

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Section: Introductionmentioning

confidence: 64%

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confidence: 99%

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

et al. 2020

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“…This lower band gap energy indicates an easier combination of DPT binding with Cu 2+ ions. 23 The transition occurred due to the complex formation of DPT with Cu 2+ ions and resulted in the formation of new peak in the UV-Vis absorption spectra. The formation energy produced by the DPT was −1113.79645660 a.u., while the complex formation energy was calculated as −2435.71832681 a.u.…”

Section: Homo-lumo Interactionsmentioning

confidence: 99%

Chemosensor Development of Cu2+ Recognition Using 1,5-Diphenylthiocarbazone: Optimization, COSMO-RS and DFT Studies

Normaya

Syuhada

Ismail

et al. 2019

J. Braz. Chem. Soc.

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“…Recently, fluorescent probes for detecting metal ions have been interested by researchers for their advantages, just like high sensitivity, briefness, and real‐time detection . So far, many fluorescent sensors are designed and synthesized for the Cd 2+ detection . However, most of them bear the problem of selectivity due to other metal ions with similar chemical structures, such as Zn 2+ , which interfere the recognition.…”

Section: Introductionmentioning

confidence: 99%

A New Fluorescent Probe for Selective Cd²⁺ Detection and Cell Imaging

Lin

Xie

Wang

et al. 2019

Zeitschrift anorg allge chemie

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Quinoline-based highly selective and sensitive fluorescent probe specific for Cd2+ detection in mixed aqueous media

Cited by 22 publications

References 32 publications

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

Chemosensor Development of Cu2+ Recognition Using 1,5-Diphenylthiocarbazone: Optimization, COSMO-RS and DFT Studies

A New Fluorescent Probe for Selective Cd²⁺ Detection and Cell Imaging

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Quinoline-based highly selective and sensitive fluorescent probe specific for Cd2+ detection in mixed aqueous media

Cited by 22 publications

References 32 publications

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

Chemosensor Development of Cu2+ Recognition Using 1,5-Diphenylthiocarbazone: Optimization, COSMO-RS and DFT Studies

A New Fluorescent Probe for Selective Cd2+ Detection and Cell Imaging

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A New Fluorescent Probe for Selective Cd²⁺ Detection and Cell Imaging