Schiff Base Compounds Derived from 5-Methyl Salicylaldehyde as Turn-On Fluorescent Probes for Al3+ Detection: Experimental and DFT Calculations
Abstract
:1. Introduction
2. Results and Discussion
2.1. Design, Synthesis, and Structural Characterization of Compounds 3a–3c
2.2. Theoretical Calculation Study for Compounds 3a–3c
2.3. Study on the Optical Properties of Compounds 3a–3c
2.3.1. Study on the Optical Properties of Compounds 3a–3c in Different Solvents
2.3.2. Study on the ACQ Properties of Compounds 3a–3c
2.4. Research on the Detection of Metal Ions with Compounds 3a–3c
2.4.1. Selective Study of Compounds 3a–3c with Metal Ions
2.4.2. Anti-Interference Study of Compounds 3a–3c with Metal Ions
2.4.3. Quantitative Identification of Al3+ by Compounds 3a–3c
2.4.4. Study on the Time Response of Probes 3a–3c to Al3+
2.4.5. The Binding Ratio and Binding Constant of Probes 3a–3c Interacting with Al3+
2.4.6. Study on pH Tolerance of Probes 3a–3c in Interaction with Al3+
2.5. Sensing Mechanism of Compounds 3a–3c to Al3+
2.5.1. 1H NMR and FT-IR Study on the Interaction Between Compounds 3a–3c to Al3+
2.5.2. DFT Study on the Interaction Between Compounds 3a–3c to Al3+
2.6. Practical Detection Application of Probes 3a–3c to Al3+
2.6.1. Application of Probes 3a–3c in Detecting Al3+ in Actual Water and Soil Samples
2.6.2. Application of Test Strips Loaded with Compounds 3a–3c for the Detection of Al3+
3. Materials and Methods
3.1. Reagents and Instruments
3.2. Synthesis
3.2.1. Synthesis of Compound 3a
3.2.2. Synthesis of Compound 3b
3.2.3. Synthesis of Compound 3c
3.3. Computational Details
3.4. Spectrophotometric Experiments
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
- Meng, S.; Liu, J.X.; Yang, Y.Y.; Mao, S.; Li, Z. Lanthanide MOFs based portable fluorescence sensing platform: Quantitative and visual detection of ciprofloxacin and Al3+. Sci. Total Environ. 2024, 922, 171115. [Google Scholar] [CrossRef]
- Zou, Y.-L.; Liu, Y.-T. A novel isophorone-based NIR fluorescent and colormetric probe for Al3+ sensing and its application for living cells and plants imaging. Spectrochim. Acta A 2024, 312, 124040. [Google Scholar] [CrossRef]
- Sun, J.Q.; Wang, Y.G.; Wang, M.D.; Wang, H.M. A bisalicylhydrazone based fluorescent probe for detecting Al3+ with high sensitivity and selectivity and imaging in living cells. Spectrochim. Acta A 2024, 322, 124784. [Google Scholar] [CrossRef]
- Selvan, G.T.; Babu, L.; Enoch, I.M.V.; Srinivasadesikan, V.; Mariselvam, R.; Kumar, A.R.; Li, X.S.; Tang, P.J.; Selvakumar, P.M.; Zhang, Z. Surface-modified gold nanoparticles: A novel chemical probe for precise fluorescent detection of aluminium (Al3+) ions; investigating DFT insights and molecular logic gate behaviour. J. Mol. Liq. 2024, 397, 124039. [Google Scholar] [CrossRef]
- Yao, B.Y.; Zhang, J.H.; Han, M.; Liang, L.; Li, X.H.; Cai, X.H.; Leng, Y.L. Two novel “turn on” fluorescent probes for the determination of Al3+ and its applications. Inorg. Chim. Acta 2023, 153, 110798. [Google Scholar] [CrossRef]
- Che, H.C.; Tian, X.K.; Wang, J.H.; Dai, C.; Nie, Y.L.; Li, Y.; Lu, L.Q. A portable and intelligent logic detector for simultaneous and in-situ detection of Al3+ and fluoride in groundwater. J. Hazard. Mater. 2023, 458, 131956. [Google Scholar] [CrossRef]
- Zhou, L.-S.; Zhang, X.-Y.; Huang, Y. High selective, sensitive, reversible and imaging application sensor for aluminium detection. J. Mol. Struct. 2024, 1310, 138357. [Google Scholar] [CrossRef]
- Mortada, W.I.; Alharthi, S. Preconcentration of aluminum by dual-cloud point extraction and its determination by inductively coupled plasma-optical emission spectrometry. Curr. Anal. Chem. 2021, 17, 1365–1372. [Google Scholar] [CrossRef]
- Mashhadizadeh, M.H.; Amoli-Diva, M. Atomic absorption spectrometric determination of Al3+ and Cr3+ after preconcentration and separation on 3-mercaptopropionic acid modified silica coated-Fe3O4 nanoparticles. J. Anal. At. Spectrom. 2013, 28, 251–258. [Google Scholar] [CrossRef]
- Ham, Y.S.; Okazaki, M.; Suzuki, S.; Nakagawa, N. Determination of total aluminum concentration in soil solution using capillary electrophoresis. Soil Sci. Plant Nutr. 2003, 49, 9–16. [Google Scholar] [CrossRef]
- Sharma, S.; Debnath, J.; Ghosh, K.S. Method for highly selective, ultrasensitive fluorimetric detection of Cu2+ and Al3+ by Schiff bases containing o-phenylenediamine and o-aminophenol. Methods 2023, 217, 27–35. [Google Scholar] [CrossRef]
- Yang, K.; Shi, S.B.; Han, S.L.; Wu, J.Y.; Li, S.C.; Zhu, R.; Tai, S.D.; Zhang, K. Europium-macrocycle based lab-on-a-molecule fluorescent probe and its multianalyte detection of phosphate and aluminum ions. Sens. Actuators B 2024, 410, 135734. [Google Scholar] [CrossRef]
- Zhang, Y.; Wang, G. A novel ethylene linkage-based covalent organic framework for turn-on fluorescence sensing for Al3+ with excellent selectivity and sensitivity. Int. J. Biol. Macromol. 2024, 262, 130195. [Google Scholar] [CrossRef]
- Ma, L.; Xia, B.Y.; Zhang, Y.Y.; Lv, J.X.; Lv, Y.G.; Zhang, X.Y. A highly sensitive fluorescent probe for the detection of Al3+ and study of its practical application. J. Mol. Liq. 2024, 1316, 138886. [Google Scholar] [CrossRef]
- Hu, Y.; Lu, L.M.; Wu, Y.X.; Li, Y.J.; Wang, F.; Chen, X.Q.; Fu, H.Y.; She, Y.B. Bifunctional ratiometric fluorescent membrane containing pyrene-based probe for visual monitoring and efficient removal of Al3+. Sens. Actuators B 2024, 413, 135860. [Google Scholar] [CrossRef]
- Liu, Y.C.; Li, N.; Zhang, Y.L.; Wang, Y. Diphenyl imidazole-based fluorescent chemosensor for Al3+ and its Al3+ complex toward water detection in food products. Food Chem. 2023, 420, 136138. [Google Scholar] [CrossRef]
- Li, M.; Li, N.; Shao, F.; Wang, R.; Chen, M.; Liu, Y.-J.; Zhao, Y.; Li, R. Synthesis of a super-low detection limit fluorescent probe for Al3+ and its application in fluorescence imaging of zebrafish and cells. Spectrochim. Acta A 2024, 308, 123676. [Google Scholar] [CrossRef]
- Bhiri, F.; Chemli, M.; Sakly, N.; Bahrouni, Y.; Wazzan, N.; Majdoub, M. New chromogenic and fluorogenic symmetric carbazole Schiff base-derivative: Synthesis, sensing performances and smartphone-assisted fluorometric assay for selective Al3+ detection in drinking water. J. Mol. Struct. 2025, 1322, 140548. [Google Scholar] [CrossRef]
- Lei, X.L.; Zou, Y.Y.; Liang, Q.J.; Xu, W.S.; Lao, S.S.; Yang, B.; Li, L.G.; Yang, L.T.; Liu, H.; Ma, L.J. An ultrasensitive 4-(diethylamino) salicylaldehyd-based fluorescence enhancement probe for the detection of Al3+ in aqueous solutions and its application in cells. J. Photochem. Photobiol. A 2022, 428, 113854. [Google Scholar] [CrossRef]
- Yasar, O.G.; Elmas, S.N.K.; Aydin, D.; Arslan, F.N. Al3+ selective ratiometric fluorescent and colorimetric chemoprobe and its practical applications in foods, test kits and smartphone. J. Photochem. Photobiol. A 2024, 447, 115238. [Google Scholar]
- Wang, S.; Liao, Y.H.; Feng, H.J.; Wu, L.Y.; He, W.Y. The studies on a fluorescent probe of Schiff base modified by 1,2,3-triazole to detecting Al3+ and living cell imaging. J. Mol. Struct. 2024, 1296, 136730. [Google Scholar] [CrossRef]
- Wang, X.M.; Li, Y.F.; Liu, L.Q.; Tan, Z.Q.; Zhou, X.H.; You, Y.J.; Wang, S. A dual-emission fluorescence coordination polymer for simultaneous quantification of Al3+ and Pb2+ in their mixtures. J. Mater. Chem. C 2024, 12, 17144–17152. [Google Scholar] [CrossRef]
- Zhao, C.; Xu, H.M.; Meng, Y.T.; Wang, Y.; Shuang, S.M.; Dong, C. Anthraquinone-based Schiff base fluorescent probe for the sequential sensing of Al3+ and pyrophosphate in a near-perfect aqueous solution and bioimaging. J. Mol. Liq. 2023, 391, 123326. [Google Scholar] [CrossRef]
- Suganthi, G.; Ajitha, R.; Babu, A.A.; Kamalesu, S.; Subramanian, R.; Arun, T.; Godlyn, A.; Nagaraj, K. Highly efficient fluorescence sensing of Al3+ ions using a sensitive carbazole based Schiff base. Inorg. Chim. Acta 2024, 161, 112150. [Google Scholar] [CrossRef]
- Zhang, Z.Y.; Wang, S.; Wang, M.X.; Li, H.M.; Liang, Q.J.; Tang, J.W.; Sun, J.; Ma, L.J.; Liu, H. An ultra-sensitive fluorescence multi-channel and colorimetric probe based on salicylaldehyde hydrazone for Al3+ recognition with a 3:1 binding ratio. J. Mater. Chem. C 2024, 12, 15144–15151. [Google Scholar] [CrossRef]
- Dev, K.; Singh, S.; Bhardwaj, S.; Kukreti, P.; Ramakanth, D.; Kumar, P.; Saini, S.; Roy, P.; Srivastava, V.C.; Ghosh, K.; et al. Solvent-selective fluorescence sensing of Mg2+ and Al3+ ions by pincer-type NNO Schiff base ligand: An experimental and DFT optimized approach. Chem.-Eur. J. 2024, 30, e202403256. [Google Scholar] [CrossRef]
- Islam, M.S.; Hoque, A.; Baig, K.M.Y.; Sarmin, M.; Kole, G.K.; Hoda, M.; Alam, M.A. A zwitterionic probe for ratiometric fluorescent detection of aluminium(III) ion in aqueous medium and its application in bioimaging. Spectrochim. Acta A 2024, 311, 124005. [Google Scholar] [CrossRef]
- Goswami, N.; Naithani, S.; Goswami, T.; Kumar, P.; Kumar, S. A quinoline derived Schiff base as highly selective ‘turn-on’ probe for fluorogenic recognition of Al3+ ion. Spectrochim. Acta A 2024, 310, 123971. [Google Scholar] [CrossRef]
- Elmas, S.N.K.; Boran, T.; Arslan, F.N.; Özhan, G.; Erdemir, S. Ultrafast and nanomolar detection of Al3+: Furazan based fluorescent chemosensor and its practices in smartphone, test kit, water samples and living-cell. Microchem. J. 2024, 200, 110444. [Google Scholar] [CrossRef]
- Jiang, Q.; Song, J.; Yang, X.Q.; Rao, X.P.; Zhao, P.; Wang, Z.L. A novel reversible fluorescent probe for sequential detection of Al3+ and HPO42− based on caffeic acid and its applicability in cell imaging. Spectrochim. Acta A 2024, 307, 123627. [Google Scholar] [CrossRef]
- Chen, S.-H.; Jiang, K.; Xiao, Y.; Cao, X.-Y.; Arulkumar, M.; Wang, Z.-Y. Recent endeavors on design, synthesis, fluorescence mechanisms and applications of benzazole-based molecular probes toward miscellaneous species. Dyes Pigm. 2020, 175, 108157. [Google Scholar] [CrossRef]
- Chen, S.-H.; Jiang, K.; Liang, Y.-H.; He, J.-P.; Xu, B.-J.; Chen, Z.-H.; Wang, Z.-Y. Fine-tuning benzazole-based probe for the ultrasensitive detection of Hg2+ in water samples and seaweed samples. Food Chem. 2023, 428, 136800. [Google Scholar] [CrossRef]
- Wang, R.Y.; Feng, X.; Feng, B.Y.; Chen, Y. Boron-mediated one-pot access to salicylaldehydes via ortho-C-H hydroxylation of benzaldehydes. RSC Adv. 2024, 14, 19922–19925. [Google Scholar] [CrossRef]
- Mohammed, A.K.; Pandikassala, A.; Sánchez, P.P.; Gaber, S.A.; Canossa, S.; Kurian, M.; Xavier, G.; He, Y.; Gándara, F.; Kurungot, S.; et al. Iron salicylaldehydate conjugated metal-organic framework for quasi solid-state supercapacitor. Chem. Eng. J. 2024, 496, 153589. [Google Scholar] [CrossRef]
- Mandi, A.; Bar, N.; Biswas, D.; Ray, A.; Ghosh, K.; Mondal, D.; Das, G.K.; Chowdhury, P. Rhodamine 6G salicylaldehyde hydrazone-Zn complex: Synthesis, characterization, photochromism, understanding, and application. J. Lumin. 2024, 271, 120611. [Google Scholar] [CrossRef]
- Sahu, M.; Ganguly, M.; Sharma, P. Recent applications of coinage metal nanoparticles passivated with salicylaldehyde and salicylaldehyde-based Schiff bases. Nanoscale Adv. 2024, 6, 4545–4566. [Google Scholar] [CrossRef] [PubMed]
- Rajalakshmi, K.; Muthusamy, S.; Lee, H.J.; Kannan, P.; Zhu, D.W.; Song, J.W.; Nam, Y.S.; Heo, D.N.; Kwon, I.; Luo, Z.B.; et al. Dual-channel fluorescent probe for discriminative detection of H2S and N2H4: Exploring sensing mechanism and real-time applications. J. Hazard. Mater. 2024, 465, 133036. [Google Scholar] [CrossRef]
- Zhou, N.; Cai, M.Y.; Zheng, S.N.; Guo, H.Y.; Yang, F.F. First organic fluorescent sensor for pesticide paclobutrazol based on tetraphenylimidazole Schiff base. Sens. Actuators B 2024, 417, 136051. [Google Scholar] [CrossRef]
- Dathees, T.J.; Narmatha, G.; Prabakaran, G.; Seenithurai, S.; Chai, J.D.; Kumar, R.S.; Prabhu, J.; Nandhakumar, R. Salicylaldehyde built fluorescent probe for dual sensing of Al3+, Zn2+ ions: Applications in latent fingerprint, bio-imaging & real sample analysis. Food Chem. 2024, 441, 138362. [Google Scholar]
- Palta, A.; Kumar, G.; Paul, K.; Luxami, V. Highly selective colorimetric and fluorescent probe for F− and P2O74− based on AIEE and dual ESIPT. J. Mol. Struct. 2024, 1316, 138880. [Google Scholar] [CrossRef]
- Dwivedi, S.K.; Arachchige, D.L.; Vohs, T.; Tang, J.N.; Usimaki, K.; Olowolagba, A.M.; Fritz, D.R.; Luck, R.L.; Werner, T.; Liu, H.Y. Near-infrared rhodol dyes bearing salicylaldehyde moieties for ratiometric pH sensing in live cells during mitophagy and under hypoxia conditions. J. Mater. Chem. B 2023, 11, 2852–2861. [Google Scholar] [CrossRef] [PubMed]
- Yang, Y.-Y.; Ma, P.-Y.; Xue, J.-H.; Yang, D.-D.; Shi, Y.-S.; Zhao, X.; Ma, Q. A highly selective fluorescent probe based on multi-binding site hydrazone chemosensor for Al3+ detection. Microchem. J. 2024, 200, 110495. [Google Scholar] [CrossRef]
- Pang, Y.L.; Meng, D.S.; Liu, J.; Duan, S.X.; Fan, J.R.; Gao, L.Y.; Long, X.S. Schiff base compounds as fluorescent probes for the highly sensitive and selective detection of Al3+ ions. Molecules 2023, 28, 3090. [Google Scholar] [CrossRef] [PubMed]
- Zhao, J.N.; Li, C.Q.; Wei, S.H.; Lu, C.W.; Zou, L.W. A multifunctional fluorescent probe based on Schiff base with AIE and ESIPT characteristics for effective detections of Pb2+, Ag+ and Fe3+. Spectrochim. Acta A 2023, 300, 122904. [Google Scholar] [CrossRef]
- Duan, N.; Ding, L.Y.; Yang, S.X.; Tian, H.Y.; Sun, B.G. A benzimidazole-based ‘turn-on’ fluorescent probe for highly sensitive detection of Fe3+/2+: Synthesis, performance, DFT calculations and applications. J. Mater. Chem. C 2024, 12, 7359–7365. [Google Scholar] [CrossRef]
- Liu, Y.L.; Li, L.; Yue, M.L.; Yang, L.; Sun, F.; Xu, G.Q.; Fu, Y.; Ye, F. A switch-on fluorescent probe for detection of mesotrione based on the straightforward cleavage of carbon-nitrogen double bond of Schiff base. Chem. Eng. J. 2022, 430, 132758. [Google Scholar] [CrossRef]
- Wang, X.Y.; Shu, J.; Ni, T.; Xu, C.X.; Tang, J.Y.; Xu, B.; Liu, X.Q.; Zhang, K.M.; Jiang, W.D. Multiple stimuli-responsive properties of coumarin-salicylaldehyde Schiff bases. Dyes Pigm. 2023, 208, 110820. [Google Scholar] [CrossRef]
- Soliman, A.I.A.; Sayed, M.; Elshanawany, M.M.; Younis, O.; Ahmed, M.; El-Dean, A.M.K.; Abdel-Wahab, A.M.A.; Wachtveitl, J.; Braun, M.; Fatehi, P.; et al. Base-free synthesis and photophysical properties of new Schiff bases containing indole moiety. ACS Omega 2022, 7, 10178–10186. [Google Scholar] [CrossRef]
- Lu, C.X.; Xu, J.W.; Song, Z.; Dai, Z.Y. Advancements in ESIPT probe research over the past three years based on different fluorophores. Dyes Pigm. 2023, 208, 110820. [Google Scholar] [CrossRef]
- Yang, M.; Mu, H.Y.; Gao, J.A.; Zhen, Q.; Wang, X.N.; Guan, X.T.; Li, H.; Li, B. Screening the optimal probe by expounding the ESIPT mechanism and photophysical properties in vis-HBX with multimodal substitutions. Molecules 2023, 28, 3090. [Google Scholar]
- Zhao, C.; Aziz, A.; Lu, W.J.; Xu, H.M.; Asif, M.; Shuang, S.M.; Dong, C. A turn-on anthraquinone-derived colorimetric and fluorometric dual-mode probe for highly selective Hg2+ determination and bioimaging in living organisms. J. Hazard. Mater. 2024, 479, 135694. [Google Scholar] [CrossRef] [PubMed]
- Anan, J.; Fosu, E.A.; Obuah, C.; Ainooson, M.K.; Aniagyei, A.; Hamenu, L.; Oppong, A.; Muller, A. A DFT and TD-DFT studies of the photosensitizing capabilities of thiophene-based dyes. Comput. Theor. Chem. 2024, 1237, 114633. [Google Scholar] [CrossRef]
- Zhao, J.; Li, Q.; Guo, M.L.; Yan, L.; Hu, G.X.; Zhu, L.X.; Yin, H.; Shi, Y. Solvent effects on the ESIPT emission of salicylaldehyde Schiff base derivative: A theoretical reconsideration. J. Mol. Liq. 2024, 408, 125265. [Google Scholar] [CrossRef]
- Queiroz, M.H.; Alves, T.V.; Rivelino, R.; Canuto, S. Influence of solvents and halogenation on ESIPT of benzimidazole derivatives for designing turn-on fluorescence probes. ACS Omega 2024, 9, 22102–22111. [Google Scholar] [CrossRef] [PubMed]
- Zhang, Z.C.; Liu, C.; Lu, Y.; Zhao, W.L.; Zhu, Q.G.; He, H.S.; Chen, Z.J.; Wu, W. In vivo fluorescence imaging of nanocarriers in near-infrared window II based on aggregation-caused quenching. J. Nanobiotechnol. 2024, 22, 488. [Google Scholar] [CrossRef]
- Jiang, K.; Chen, S.-H.; Luo, S.-H.; Pang, C.-M.; Wu, X.-Y.; Wang, Z.-Y. Concise design and synthesis of water-soluble fluorescence sensor for sequential detection of Zn(II) and picric acid via cascade mechanism. Dyes Pigm. 2019, 167, 164–173. [Google Scholar] [CrossRef]
- Sidqi, M.E.; Aziz, A.A.A.; Abolehasan, A.E.; Sayed, M.A. Photochemical processing potential of a novel Schiff base as a fluorescent probe for selective monitoring of Al3+ ions and bioimaging in human cervical cancer HeLa cells. J. Photochem. Photobiol. A 2022, 424, 113616. [Google Scholar] [CrossRef]
- Zhao, C.; Xu, H.M.; Zhang, X.R.; Meng, Y.T.; Shuang, S.M.; Dong, C. Anthraquinone-metal complex fluorescence sensing platform for monitoring PPi mediated by Al3+ and bioimaging. J. Mol. Struct. 2024, 1308, 138022. [Google Scholar] [CrossRef]
- Sultana, T.; Mahato, M.; Tohora, N.; Ahamed, S.; Das, S.K. An azine-based chromogenic, fluorogenic probe for specific cascade detection of Al3+ and PO43− ions. J. Photochem. Photobiol. A 2023, 444, 114951. [Google Scholar] [CrossRef]
- Xing, Z.Y.; Wang, J.L.; Huang, J.H.; Chen, X.F.; Zong, Z.A.; Fan, C.B.; Huang, G.M. A significant fluorescence turn-on probe for the recognition of Al3+ and its application. Molecules 2022, 27, 2569. [Google Scholar] [CrossRef]
- Li, L.; Zhao, J.N.; Lue, C.W. ESIPT performance bis-Schiff base for multifunctional detection of Pb2+, Mg2+ and Al3+ ions through “turn-on” response and its biological application. Res. Chem. Intermed. 2024, 50, 5017–5038. [Google Scholar] [CrossRef]
- Chen, Z.-H.; Chen, Z.-J.; Zeng, Y.; Liang, Y.-T.; Guo, J.-L.; Yang, S.-H.; Wang, Z.-Y. Multifunctional N-fused fluorescent probes for detection of iron ions and nitro explosives. Spectrochim. Acta A 2025, 326, 125281. [Google Scholar] [CrossRef] [PubMed]
- Mishra, S.; Mamidi, P.; Chattopadhyay, S.; Singh, A.K. Economically viable multi-responsive probes for fluorimetric detection of trace levels of Ga3+, Al3+ and PPi in near aqueous medium. J. Photochem. Photobiol. A 2023, 434, 114225. [Google Scholar] [CrossRef]
- Zhao, L.-X.; He, X.-L.; Xie, K.-B.; Hu, J.-J.; Deng, M.-Y.; Zou, Y.-L.; Gao, S.; Fu, Y.; Ye, F. A novel isophorone-based fluorescent probe for recognition of Al3+ and its bioimaging in cells and plants. Spectrochim. Acta A 2023, 385, 121882. [Google Scholar] [CrossRef] [PubMed]
- Chen, Z.-H.; Chen, Z.-J.; Li, W.-X.; Zeng, Y.; Lin, J.-Q.; Tao, G.-S.; Wang, Z.-Y. Synthesis of a novel N-fused ring based organic molecule probe and its detection of iron. Inorg. Chim. Acta 2024, 163, 112381. [Google Scholar] [CrossRef]
- Pan, W.Y.; Yang, X.Y.; Wang, Y.S.; Wu, L.; Liang, N.; Zhao, L.S. AIE-ESIPT based colorimetric and “OFF-ON-OFF” fluorescence Schiff base sensor for visual and fluorescent determination of Cu2+ in an aqueous media. J. Photochem. Photobiol. A 2021, 420, 113506. [Google Scholar] [CrossRef]
- Sayed, M.; Kamal, A.M.; Ahmed, M.M.; Hassanien, R. Synthesis of some new heterocyclic compounds containing indole moiety. Eur. Chem. Bull. 2017, 6, 171–176. [Google Scholar] [CrossRef]
- Jia, W.G.; Zhang, H.; Zhang, T.; Xie, D.; Ling, S.; Sheng, E.H. Half-sandwich ruthenium complexes with Schiff-base ligands: Syntheses, characterization, and catalytic activities for the reduction of nitroarenes. Organometallics 2016, 35, 503–512. [Google Scholar] [CrossRef]
Samples | Al3+ Added (10−5 M) | Al3+ Found (10−5 M) | RSD (%, n = 3) | Recovery (%) |
---|---|---|---|---|
Distilled water | 1 | 0.98 | 0.14 | 98 |
2 | 1.99 | 1.53 | 99.5 | |
4 | 3.99 | 1.69 | 99.8 | |
Tap water | 1 | 0.97 | 0.88 | 97 |
2 | 1.97 | 0.19 | 98.5 | |
4 | 3.92 | 2.34 | 98 | |
River water | 1 | 1.05 | 1.22 | 105 |
2 | 1.99 | 3.09 | 99.5 | |
4 | 4.02 | 2.62 | 100.5 | |
Soil | 1 | 1.01 | 0.81 | 101 |
2 | 2.03 | 2.30 | 101.5 | |
4 | 4.10 | 1.35 | 102.5 | |
Equation | y = 107.75x + 64.17 |
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content. |
© 2025 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Li, H.-Q.; Yang, S.-H.; Li, Y.; Ye, W.-X.; Liao, Z.-Y.; Lu, J.-Q.; Wang, Z.-Y. Schiff Base Compounds Derived from 5-Methyl Salicylaldehyde as Turn-On Fluorescent Probes for Al3+ Detection: Experimental and DFT Calculations. Molecules 2025, 30, 1128. https://doi.org/10.3390/molecules30051128
Li H-Q, Yang S-H, Li Y, Ye W-X, Liao Z-Y, Lu J-Q, Wang Z-Y. Schiff Base Compounds Derived from 5-Methyl Salicylaldehyde as Turn-On Fluorescent Probes for Al3+ Detection: Experimental and DFT Calculations. Molecules. 2025; 30(5):1128. https://doi.org/10.3390/molecules30051128
Chicago/Turabian StyleLi, Huan-Qing, Shi-Hang Yang, Yun Li, Wan-Xin Ye, Zi-Yu Liao, Jia-Qian Lu, and Zhao-Yang Wang. 2025. "Schiff Base Compounds Derived from 5-Methyl Salicylaldehyde as Turn-On Fluorescent Probes for Al3+ Detection: Experimental and DFT Calculations" Molecules 30, no. 5: 1128. https://doi.org/10.3390/molecules30051128
APA StyleLi, H.-Q., Yang, S.-H., Li, Y., Ye, W.-X., Liao, Z.-Y., Lu, J.-Q., & Wang, Z.-Y. (2025). Schiff Base Compounds Derived from 5-Methyl Salicylaldehyde as Turn-On Fluorescent Probes for Al3+ Detection: Experimental and DFT Calculations. Molecules, 30(5), 1128. https://doi.org/10.3390/molecules30051128