Synthesis and photophysical investigation of (BTHN) Schiff base as off-on Cd2+ fluorescent chemosensor and its live cell imaging

Khan, Salman A.; Ullah, Qasim; Almalki, Abdulraheem S. A.; Kumar, Sanjay; Obaid, Rami J.; Alsharif, Meshari A.; Alfaifi, Sulaiman Y. M.; Hashmi, Authar Adil

doi:10.1016/j.molliq.2021.115407

Cited by 52 publications

(36 citation statements)

References 34 publications

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“…At higher temperatures, the substance begins to lose weight rapidly (see Figure 2). In 13 C NMR spectra carbonyl group demonstrates typical signal about 182-190 ppm, but aromatic carbon atoms show multiple signals at 110-150 ppm.…”

Section: Peer Review 3 Of 16mentioning

confidence: 99%

“…1 H NMR spectra were recorded on Bruker equipment, operating at 400 MHz in CDCl 3 or DMSO-d 6 (with TMS as internal standard) at ambient temperature. 13 C NMR spectra were run in the same instrument at 100 MHz using the solvent peak as internal reference.…”

Section: Materials and Basic Measurementsmentioning

confidence: 99%

“…Heterocyclic azomethines, which are ion-active "naked-eye" switches of spectral properties in the presence of fluorine, acetate, and dihydrophosphate ions, are described by Popova et al [12]. Some of the heteroaromatic imines can act as chemosensors for cations [13]. A variety of azomethine derivatives bearing heterocyclic ring have been known to show a wide range of biological activities including antioxidant [14], antibacterial [3], antifungal [15], analgesic [16], and antitumor [17] activity.…”

Section: Introductionmentioning

confidence: 99%

“…H NMR (400 MHz, DMSO) δ 12.01 (1H, s, NH), 8.99 (1H, dd, J = 8.0, 1.1 Hz), 8.72 (1H, d, J = 8.0 Hz), 8.66 (1H, dd, J = 6.7, 1.1 Hz), 8.57 (1H, d, J = 8.0 Hz), 8.55 (1H, s), 8.31 (1H, dd, J = 7.8, 1.1 Hz),7.89 (1H, t, J = 7.8 Hz),7.82 (1H, td, J = 7.5, 1.1 Hz),7.57 (1H, t, J = 7.5 Hz),7.46 (1H, d, J = 8.0 Hz), 7.17 (1H, s), 6.85 (1H, d, J = 4.2 Hz), 6.28 (1H, d, J = 6.7 Hz);13 C NMR (100 MHz, DMSO) δ 183.2, 151.7, 151.5, 136.5, 134.3, 132.4, 131.4, 130.2, 130.1, 129.2, 128.3, 128.0, 127.7, 127.1,126.6, 125.5, 124.1, 122.9, 118.3, 114.3, 110.7; FTIR (KBr) ν max 3298, 3044, 1640, 1610, 1564, 1505, 1458, 1382, 1302, 1280, 1086, 1042, 970, 856, 780, 734, 602 cm −1 EIMS m/z 322 [M] + (89), 321 (100), 292 (14), 265 (8), 239 (6), 227 (12), 201 (18), 200 (22), 161 (14), 147 (16).3-[N-(Pyridin-4-ylmethylidene)amino]benzo[de]anthracen-7-one (2b). The product was obtained as an orange crystalline solid with a yield of 77%; mp 260-261 • C; 1 H NMR (400 MHz, DMSO) δ 8.95 (1H, s), 8.82-8.90 (4H, m), 8.72 (1H, dd, J = 7.0, 1.2 Hz), 8.66 (1H, d, J = 7.8 Hz), 8.36 (1H, dd, J = 7.8, 1.6 Hz), 8.02-8.07 (2H, m), 7.97 (1H, t, J = 7.8 Hz), 7.89 (1H, td, J = 7.8, 1.6 Hz), 7.62-7.68 (2H, m); 13 C NMR (100 MHz, DMSO) δ 189.3, 158.9, 150.9, 149.6, 142.5, 135.9, 133.4, 131.1, 130.7, 130.4, 128.4, 128.3, 128.1, 124.6, 122.8, 122.4, 113.5; FTIR (KBr) ν max 3028, 1640, 1595, 1569, 1382, 1317, 1280, 1218, 1084, 839, 781, 746, 701 cm −1 ; EIMS m/z 334 [M] + (100), 256 (16), 202 (12), 201 (27), 200 (25).…”

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confidence: 99%

“…[N-(Furan-2-ylmethylidene)amino]benzo[de]anthracen-7-one (2f). The product was obtained as a dark yellow powder with a yield of 70%; mp 221-222 • C;1 H NMR (400 MHz, CDCl 3 ) δ 8.77 (1H, dd, J = 8.2, 1.3 Hz), 8.73 (1H, d, J = 8.0 Hz), 8.64 (1H, dd, J = 7.3, 1.3 Hz), 8.56 (1H, d, J = 8.2 Hz), 8.29 (1H, dd, J = 7.9, 1.5 Hz), 8.02 (1H, d, J = 1.8 Hz), 7.88 (1H, dd, J = 8.2, 7.3 Hz), 7.81 (1H, ddd, J = 8.3, 7.1, 1.5 Hz), 7.57 (1H, ddd, J = 8.0, 7.1, 1.0 Hz), 7.48 (1H, d, J = 8.0 Hz), 7.31 (1H, dd, J = 3.5, 0.8 Hz), 6.75 (1H, dd, J = 3.5, 1.8 Hz);13 C NMR (100 MHz, DMSO) δ 183.2, 152.4, 150.7, 150.2, 149.6, 147.8, 136.3, 134.3, 131.8, 130.2, 128.8, 128.6, 128.1, 127.9, 127.7, 127.1, 126.8, 124.2, 124.0, 119.2, 114.7, 113.3; FTIR (KBr) ν max 3041, 1646, 1622, 1567, 1477, 1383, 1011, 776, 745, 702, 591 cm −1 ; EIMS m/z 324 (25), 323 [M] + (100), 294 (25), 200 (23), 161(12).General Procedure for synthesis of amines 3a-f: Dissolve 0.5 mmol of the corresponding azomethine 2a-f in 15-20 mL of dimethylformamide and add 0.5 mmol of NaBH 4 in small portions over 15 min. Add 2-3 mL of methanol dropwise to the solution prepared at room temperature.…”

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Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy

et al. 2021

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New substituted azomethines of benzanthrone with heterocyclic substituents were synthesized by condensation reaction of 3-aminobenzo[de]anthracen-7-one with appropriate aromatic aldehydes. The resulting imines were reduced with sodium borohydride to the corresponding amines, the luminescence of which is more pronounced in comparison with the initial azomethines. The novel benzanthrone derivatives were characterized by NMR, IR, MS, UV/Vis, and fluorescence spectroscopy. The structure of three dyes was studied by the X-ray single crystal structure analysis. The solvent effect on photophysical behaviors of synthesized imines and amines was investigated. The obtained compounds absorb at 420–525 nm, have relatively large Stokes shifts (up to 150 nm in ethanol), and emit at 500–660 nm. The results testify that emission of the studied compounds is sensitive to the solvent polarity, exhibiting negative fluorosolvatochromism for the synthesized azomethines and positive fluorosolvatochromism for the obtained amines. The results obtained indicate that the synthesized compounds are promising as luminescent dyes.

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Section: Materials and Basic Measurementsmentioning

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Section: Introductionmentioning

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Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy

et al. 2021

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Heterocyclic fluorescent Schiff base chemosensors for the detection of Fe(III) and Cu(II) ions

Sambamoorthy,

Thamaraichelvan,

Karikalan

et al. 2024

Luminescence

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Two new Schiff bases were synthesized from 1‐(2,4‐dihydroxyphenyl)ethanone and pyridine derivatives. Both compounds were characterized using infrared, UV–Vis., 1H NMR, 13C NMR and mass spectral studies. Density functional theory (DFT) calculations were performed for both the Schiff bases with 6‐31G(d, p) as the basis set. Vibrational frequencies calculated using the theoretical method were in good agreement with the experimental values. Both the Schiff bases were highly fluorescent in nature. The cation‐recognizing profile of the compounds was investigated in aqueous methanol medium. The Schiff base 4‐(1‐(pyridin‐4‐ylimino)ethyl)benzene‐1,3‐diol (PYEB) was found to interact with Fe(III) and Cu(II) ions, whereas the Schiff base 4,4′‐((pyridine‐2,3‐diylbis(azanylylidene))bis(ethan‐1‐yl‐1‐ylidene))bis(benzene‐1,3‐diol) (PDEB) was found to detect Cu(II) ions. The mechanism of recognition was established as combined excited state intramolecular proton transfer (ESIPT)–chelation‐enhanced fluorescence (CHEF) effect and chelation‐enhanced quenching (CHEQ) process for the detection of Fe(III) and Cu(II) ions, respectively. The stability constant of the metal complexes formed during the sensing process was determined. The limit of detection for Fe(III) and Cu(II) ions with respect to Schiff base PYEB was found to be 1.64 × 10−6 and 2.16 × 10−7 M, respectively. With respect to Schiff base PDEB, the limit of detection for Cu(II) ion was found to be 4.54 × 10−4 M. The Cu(II) ion sensing property of the Schiff base PDEB was applied in bioimaging studies for the detection of HeLa cells.

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A novel thiourea‐based fluorescent turn‐on sensor for rapidly detecting hypochlorite through a desulfurization reaction

Choi,

Kim,

Kim

2024

Bulletin Korean Chem Soc

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Excess hypochlorite (ClO−) is harmful to living organisms and can cause various oxidative diseases in the human body. Owing to the toxicity of ClO−, the development of efficient fluorescence sensors to track ClO− is necessary. In this work, we report a novel thiourea‐based fluorescent turn‐on sensor 1‐(9‐ethyl‐9H‐carbazol‐3‐yl)‐3‐(naphthalen‐1‐yl)thiourea (ECNT) for recognizing ClO−. ECNT can detect ClO− with high selectivity, relatively low interference with other analytes, and a significantly fast response time (<1 s) through a desulfurization reaction. The detection limit of ECNT for ClO− is calculated as 5.59 μM. Of note, ECNT is a chemosensor that reacts the fastest with ClO− among the reported thiourea‐based fluorescence turn‐on sensors for detecting ClO−. The response mechanism of ECNT to ClO− is demonstrated through 1H NMR titration, ESI mass, and density functional theory calculations.

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Synthesis and photophysical investigation of (BTHN) Schiff base as off-on Cd2+ fluorescent chemosensor and its live cell imaging

Cited by 52 publications

References 34 publications

Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy

Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy

Heterocyclic fluorescent Schiff base chemosensors for the detection of Fe(III) and Cu(II) ions

A novel thiourea‐based fluorescent turn‐on sensor for rapidly detecting hypochlorite through a desulfurization reaction

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