Receptor‐Spacer‐Fluorophore Based Coumarin‐Thiosemicarbazones as Anion Chemosensors with <i>“Turn on”</i> Response: Spectroscopic and Computational (DFT) Studies

Islam, Muhammad; Hameed, Abdul; Ayub, Khurshid; Naseer, Muhamamd Moazzam; Hussain, Javid; Alharthy, Rima D.; Asari, Asnuzilawati; Ludwig, Ralf; Rashida, Mariya al; Shafiq, Zahid

doi:10.1002/slct.201801035

Cited by 22 publications

(13 citation statements)

References 35 publications

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“…Specifically, comparing 1 and 4, their associations constant were 1.64 × 10 4 and 1.63 × 10 5 respectively where the receptor unit are the same only the chromophoric units are different (Table 1 ). Similar substituent effect have been reported recently 42 . Among the nitro-based receptors, compound 3 has the highest association constant which could be attributed to the push effect of the tertiary amine group on the receptor.…”

Section: Resultssupporting

confidence: 90%

“…All compound ( 1–6 ) exhibit capability for sensing for F − , AcO − , and CN − but derivatives 3 and 5 showed sensing responses to AcO − anions with distinct spectral patterns. Some recent studies have reported fluoro-substituted phenyl giving a curved conformation to the compounds 42 . A curved conformations where a cavity is formed limits the receptor/anions interaction by allowing the anions to approach for the –N–H proton based on the anion size 44 .…”

Section: Resultsmentioning

confidence: 99%

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2-Nitro- and 4-fluorocinnamaldehyde based receptors as naked-eye chemosensors to potential molecular keypad lock

Islam

Shafiq

Mabood

et al. 2021

Sci Rep

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New-generation chemosensors desire small organic molecules that are easy to synthesise and cost-effective. As a new interdisciplinary area of research, the integration of these chemosensors into keypad locks or other advanced communication protocols is becoming increasingly popular. Our lab has developed new chemosensor probes that contain 2-nitro- (1–3) and 4-fluoro-cinnamaldehyde (4–6) and applied them to the anion recognition and sensing process. Probes 1–6 are colorimetric sensors for naked-eye detection of AcO−/CN−/F−, while probes 4–6 could differentiate between F− and AcO−/CN− anions in acetonitrile. Using the density functional theory (DFT), it was found that probes 1–6 acted as effective chemosensors. By using Probe 5 as a chemosensor, we explored colorimetric recognition of multiple anions in more detail. Probe 5 was tested in combination with a combinatorial approach to demonstrate pattern-generation capability and its ability to distinguish among chemical inputs based on concentration. After pattern discrimination using principal component analysis (PCA), we examined anion selectivity using DFT computation. In our study, probe 5 demonstrates excellent performance as a chemosensor and shows promise as a future molecular-level keypad lock system.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

2-Nitro- and 4-fluorocinnamaldehyde based receptors as naked-eye chemosensors to potential molecular keypad lock

Islam

Shafiq

Mabood

et al. 2021

Sci Rep

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“…The molecular orbital (MO) energy level and distribution of the Lansoprazole was carried out by density functional theory (DFT) calculation at the B3LYP/6-311+G(2d,2p) level (Ishtiaq et al, 2016 ; Iqbal et al, 2018 ; Isaac et al, 2018 ; Islam et al, 2018 ). As we can see from Figure 7 , the electron clouds of LUMO+1, LUMO+2 level of energy for chemosensor L were mainly distributed on the pyridine, and for LUMO level cloud was distributed on the C=N bond of benzimidazole group.…”

Section: Resultsmentioning

confidence: 99%

Lansoprazole-Based Colorimetric Chemosensor for Efficient Binding and Sensing of Carbonate Ion: Spectroscopy and DFT Studies

et al. 2021

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The new benzimidazole based receptor Lansoprazole has been used to detect carbonate anion by naked-eye and Uv-Vis spectroscopy. This receptor revealed visual changes with CO32- anion in ethanol. No detectable color changes were observed upon the addition of any other tested anions. The lansoprazole chemosensor selectively recognizes CO32- ion over the other interference anions in the ethanol, followed by deprotonation and reflected 1:1 complex formation between the receptor and the carbonate ion. Lansoprazole exhibits splendid selectivity toward carbonate ion via a visible color change from colorless to yellow with a detection limit of 57 μM. The binding mode of CO32- to receptor L is supported by Density Functional Theory calculation. Moreover, this receptor shows a practical visible colorimetric test strip for the detection of carbonate ions. The transition states calculation demonstrates the occurrence of reaction from L to L-CO32- after overcoming an energy barrier of 10.1 kcal/mol, and there is considerable interaction energy between L and CO32- (94.9 kJ/mol), both of which confirmed that receptor L has high sensitivity and selectivity to the carbonate ion. The theoretical studies were performed to acquire an electronic description of the complexation mechanism by CO32- as well as to study bonding and structure in the complex. The optimized structures and binding mechanisms were supported with a high correlation and agreement by spectroscopy and DFT calculations.

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“…It is known that N H proton abstraction by F anion can enhance fluorescence intensity which is one of the requirements of improving the sensitivity. [39] The deprotonation of BNDP in the presence of F anion is evaluated to examine whether the deprotonated anion form of the BNDP (BNDP À ) can interact with the gases to produce an observable optical response. The structures of BNDP, F anion-attached complex, and BNDP À are optimized using the M06À2X/6-31 + G(d) method.…”

Section: Generation Of Bndp àmentioning

confidence: 99%

Fluoride ion‐induced gas sensor based on the dipyrromethene boron difluoride derivative: A theoretical investigation

Wang

2021

J of Physical Organic Chem

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In this study, density functional theory (DFT) studies were performed to evaluate the response of the BODIPY derivative (BNDP À ) as a gas sensor toward CO 2 , COS, SO 2 , SO 3 , H 2 S, and NH 3 . The sensing ability of the BNDP À interacting with the gases was described in terms of geometric, electronic, and optical properties. Results showed that the strong interactions between BNDP À and the gases were ascribed to the short linkage distance and the large variation of geometries. The AIM analysis was used to shed light on the sensor mechanisms of the BNDP À toward the gases. The spectroscopic properties, UV-vis absorption and fluorescence emission spectra, revealed the behavior of the interaction of BNDP À with these gases. These parameters, including the compositions of the frontier molecular orbitals and the values of orbital energy gaps, indicated that the BNDP À had good sensitivity toward CO 2 , COS, SO 2 , and SO 3 .

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Receptor‐Spacer‐Fluorophore Based Coumarin‐Thiosemicarbazones as Anion Chemosensors with “Turn on” Response: Spectroscopic and Computational (DFT) Studies

Cited by 22 publications

References 35 publications

2-Nitro- and 4-fluorocinnamaldehyde based receptors as naked-eye chemosensors to potential molecular keypad lock

2-Nitro- and 4-fluorocinnamaldehyde based receptors as naked-eye chemosensors to potential molecular keypad lock

Lansoprazole-Based Colorimetric Chemosensor for Efficient Binding and Sensing of Carbonate Ion: Spectroscopy and DFT Studies

Fluoride ion‐induced gas sensor based on the dipyrromethene boron difluoride derivative: A theoretical investigation

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