The Synthesis and Anion Recognition Property of  Symmetrical Chemosensors Involving Thiourea Groups:  Theory and Experiments

Shang, Xuefang; Yang, Zhenhua; Fu, Junjiang; Zhao, Peipei; Xu, Xiufang

doi:10.3390/s151128166

Cited by 10 publications

(7 citation statements)

References 34 publications

(34 reference statements)

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“…A range of different compounds such as acridinium, 2 quinolone, 6 and urea/thiourea-based 7 receptors have been reported as chemosensors in anion detection via addition, substitution, or photo-induced electron transfer mechanisms. 1 Ion detection for anions such as halides (F − , Cl − , Br − , I − ), acetate (OAc − ), sulfate, chlorate, cyanide and thiocyanate carries much analytical importance.…”

Section: Introductionmentioning

confidence: 99%

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

et al. 2018

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The use of small molecules as chemosensors for ion detection is rapidly gaining popularity by virtue of the advantages it offers over traditional ion sensing methods. Herein we have synthesized a series of acridine(1,8)diones (7a-7l) and explored them for their potential to act as chemosensors for the detection of various anions such as fluoride (F À ), acetate (OAc À ), bromide (Br À ), iodide (I À ), bisulfate (HSO 4 À ), chlorate (ClO 3 À ), perchlorate (ClO 4 À ), cyanide (CN À ), and thiocyanate (SCN À ). Acridinediones were found to be highly selective chemosensors for fluoride ions only. To investigate in detail the mechanism of selective fluoride ion sensing, detailed spectroscopic studies were carried out using UVvisible, fluorescence and 1 H NMR spectroscopy. Fluoride mediated (NH) proton abstraction of acridinedione was found to be responsible for the observed selective fluoride ion sensing. Quantum mechanical computational studies, using time dependent density functional theory (TDDFT) were also carried out, whereupon comparison of acridinedione interaction with fluoride and acetate ions explained the acridinedione selectivity for the detection of fluoride anions. Our results provide ample evidence and rationale for further modulation and exploration of acridinediones as non-invasive chemosensors for fluoride ion detection in a variety of sample types.An oven dried round bottom ask was charged with N-alkyl (Me/ Et) morpholine (1 g, 10 mmol, 1 equiv.) and toluene (5 mL). Subsequently, corresponding alkyl (C 5 , C 7 ) bromide (1.5 equiv.) Fig. 8 Overlay UV-vis absorption spectrum of 7i and fluoride complex 7i-F À , calculated at TD-B3LYP/6-31G(d,p).This journal is

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Section: Introductionmentioning

confidence: 99%

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

et al. 2018

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“…The selectivity studies for receptor (L) included interfering ions and ions under investigation, as described in literature [43]. Figure 4 visually represents these experiments, which were conducted with the addition of 5 equivalent quantities of copper (II), silver (I), uoride, and cyanide ions in both matrixes.…”

Section: Resultsmentioning

confidence: 99%

Ion sensing with a calix[4]arene bifunctional receptor with thiosemicarbazone moieties and naphthalene chromophore

Gómez-Machuca,

Quiroga-Campano,

Pessoa-Mahana

et al. 2024

J Incl Phenom Macrocycl Chem

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We have developed a chemosensor using calix [4]arene, which features a thiosemicarbazone binding unit and a naphthalene chromogenic group. Our objective was to understand the intricate binding a nity of these chemosensors towards a diverse range of anions and cations using UV-Visible, HNMR and IR spectroscopic techniques. We show that the chemosensor forms complexes with Ag(I), Cu (II), CN − and F − ions. To understand the complexation behavior, our analysis provides information on the interaction patterns between the receptors and the ions. The sulfur and imine nitrogen on the thiosemicarbazone substituent are vital sites of engagement for cation ions, as evidenced by the observed changes in IR.Studies with anions in HNMR indicate the participation of the thiosemicarbazone hydrogens in the interaction. The interactions that take place during complex formation lead to changes in the color of the solution or solid complex. Our study improves the understanding of molecular recognition in this chemosensor, emphasizing its potential for ion-selective detection.

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“…[25][26][27] A recent study with quinoline based probe has described the deprotonation mechanism with fluoride and acetate anions to induce changes in observed absorption/fluorescence pattern. 24 Another anion sensing study with 9alkoxy acridinium has demonstrated the nucleophilic addition of anions (F -/AcO¯) at C9 position of acridinium ring causing de-aromatization, consequently inducing drastic changes in absorption/fluorescence signals of acridinium moiety.…”

Section: Resultsmentioning

confidence: 99%

Novel quinoxaline based chemosensors with selective dual mode of action: nucleophilic addition and host–guest type complex formation

et al. 2016

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§ Shared first author(contributed equally) * AbstractNew quinoxalinium salts 1-5 as chemosensors have been exploited via naked eye, UV-Vis absorption, fluorescence quenching and 1 H NMR experiments. New sensors 1-5 showed dual mode, nucleophilic addition and host-guest type complex towards anion (F¯, AcO¯ and ascorbate) detection. Small anions (F¯/AcO¯) showed nucleophilic addition at C2 position of quinoxalinium cation, while larger anion (ascorbate), revealed the formation of host-guest type complex due to steric hindrance posed by C3 of phenyl ring. Nucleophilic addition of small anions (F¯/AcO¯) leads to de-aromatization of quinoxalinium cation. However in the case of larger anion, ascorbate, host-guest type complex formation induces changes in absorption/fluorescence signals of quinoxalinium moiety. This selective binding has been confirmed on the basis of 1 H NMR spectroscopic technique, whereupon nucleophilic addition of small anions (F¯/AcO¯) was confirmed by monitoring characteristic proton NMR signals of H a and methylene protons (CH 2 ), which were clearly shifted in case of fluoride and acetate ions addition confirming de-aromatization and nucleophilic addition. Whereas no such peak shifting was observed in case of ascorbate ion addition confirming non-covalent addition of ascorbate.Theoretical insight into the selectivity and complexation behavior of ascorbate ion with quinoxaline moiety is gained through density functional theory (DFT) calculations. Moreover, the absorption properties of these complexes are modeled theoretically, and compared with the experimental data. In addition, thermal decomposition of sensor (1 and 2) has been studied by the means of differential scanning calorimetry (DSC), thermogravimetry (TG), and differential thermogravimetry (DTG) to signify their utility at variable temperature.

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The Synthesis and Anion Recognition Property of Symmetrical Chemosensors Involving Thiourea Groups: Theory and Experiments

Cited by 10 publications

References 34 publications

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

Ion sensing with a calix[4]arene bifunctional receptor with thiosemicarbazone moieties and naphthalene chromophore

Novel quinoxaline based chemosensors with selective dual mode of action: nucleophilic addition and host–guest type complex formation

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