PHENYLETHYLAMINE DERIVATIVE OF CALIX[4]ARENE SCHIFF BASE FOR FLUOROMETRIC DETECTION OF ZINC ION

Year 2023, , 748 - 757, 01.09.2023

Egemen Özçelik , Clever Ng'andu , Begüm Tabakcı , Mustafa Tabakcı

https://doi.org/10.36306/konjes.1299268

Cited By: 2

Abstract

As a Zn2+ fluorescent probe, we have designed and synthesized a new type of calixarene Schiff-base ligand (L) possessing a 1-phenylethylamine group as the fluorophore and the receptor. As only Zn2+ caused a significant increase in fluorescence emission intensity at 480 nm and the limit of detection (LOD) reached 4.8 x 10-7 M, the synthesized fluorescent probe L demonstrated high selectivity and sensitivity towards Zn2+ compared to other metal ions. In addition, the formation of a 1:1 complex between probe L and Zn2+ was determined. As a consequence, it was determined that probe L can be utilized for the detection and monitoring of Zn2+ in the environment.

Keywords

Calixarene, Schiff Base, Fluorometric Detection, Zinc, Sensor

References

• A. Kim, J. H. Kang, H. J. Jang, and C. Kim, "Fluorescent detection of Zn (II) and In (III) and colorimetric detection of Cu (II) and Co (II) by a versatile chemosensor," Journal of industrial and engineering chemistry, vol. 65, pp. 290-299, 2018.
• S. Sakunkaewkasem et al., "Dual-analyte fluorescent sensor based on [5] helicene derivative with super large stokes shift for the selective determinations of Cu2+ or Zn2+ in buffer solutions and its application in a living cell," ACS sensors, vol. 3, no. 5, pp. 1016-1023, 2018.
• J. Briffa, E. Sinagra, and R. Blundell, "Heavy metal pollution in the environment and their toxicological effects on humans. Heliyon," ed: Elsevier Ltd, 2020.
• C. Andreini, L. Banci, I. Bertini, and A. Rosato, "Zinc through the three domains of life," Journal of proteome research, vol. 5, no. 11, pp. 3173-3178, 2006.
• M. P. Cuajungco, M. S. Ramirez, and M. E. Tolmasky, "Zinc: multidimensional effects on living organisms," Biomedicines, vol. 9, no. 2, p. 208, 2021.
• A. M. Hessels and M. Merkx, "Genetically-encoded FRET-based sensors for monitoring Zn2+ in living cells," Metallomics, vol. 7, no. 2, pp. 258-266, 2015.
• L. Maxfield, S. Shukla, and J. S. Crane, "Zinc deficiency," in StatPearls [Internet]: StatPearls Publishing, 2021.
• T. S. Singh, P. C. Paul, and H. A. Pramanik, "Fluorescent chemosensor based on sensitive Schiff base for selective detection of Zn2+," Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 121, pp. 520-526, 2014.
• B. L. Vallee and K. H. Falchuk, "The biochemical basis of zinc physiology," Physiological reviews, vol. 73, no. 1, pp. 79-118, 1993.
• H. Kaur and N. Garg, "Zinc toxicity in plants: a review," Planta, vol. 253, no. 6, p. 129, 2021.
• L. M. Plum, L. Rink, and H. Haase, "The essential toxin: impact of zinc on human health," International journal of environmental research and public health, vol. 7, no. 4, pp. 1342-1365, 2010.
• L. Chen et al., "A Schiff-based AIE fluorescent probe for Zn(2+) detection and its application as "fluorescence paper-based indicator"," Spectrochim Acta A Mol Biomol Spectrosc, vol. 268, p. 120704, Mar 5 2022.
• D. Musib, M. K. Raza, S. S. Devi, and M. Roy, "A reversible, benzothiazole-based “Turn-on” fluorescence sensor for selective detection of Zn2+ ions in vitro," Journal of Chemical Sciences, vol. 132, no. 1, 2020.
• X. Wei, L. Bu, W. Tang, S. Zhao, and Y. Xie, "Selective and sensitive fluorescence “turn-on” Zn2+ probes based on combination of anthracene, diphenylamine and dipyrrin," Science China Chemistry, vol. 60, no. 9, pp. 1212-1218, 2017.
• M. Kumar, A. Kumar, M. K. Singh, S. K. Sahu, and R. P. John, "A novel benzidine based Schiff base “turn-on” fluorescent chemosensor for selective recognition of Zn2+," Sensors and Actuators B: Chemical, vol. 241, pp. 1218-1223, 2017.
• P. S. Hariharan and S. P. Anthony, "Selective turn-on fluorescence for Zn(2+) and Zn(2+)+Cd(2+) metal ions by single Schiff base chemosensor," Anal Chim Acta, vol. 848, pp. 74-79, Oct 27 2014.
• G. Xu, S. J. Ma, H. H. Zhang, J. Jing, X. H. Chen, and X. P. Zhang, "A Fluorescent Probe Based on the Hydrazone Schiff Base for the Detection of Zn(2+) and its Application on Test Strips," J Fluoresc, Jan 9 2023.
• F. Bie et al., "A cyanobiphenyl-based ratiometric fluorescent sensor for highly selective and sensitive detection of Zn2+," Inorganica Chimica Acta, vol. 508, 2020.
• J. Liu et al., "Two Schiff-base fluorescence probes based on triazole and benzotriazole for selective detection of Zn2+," Sensors and Actuators B: Chemical, vol. 227, pp. 296-303, 2016.
• J. Yang et al., "A novel tetrahydroquinazolin-2-amine-based high selective fluorescent sensor for Zn2+ from nopinone," Tetrahedron, vol. 72, no. 30, pp. 4503-4509, 2016.
• R. Behura et al., "A Schiff base luminescent chemosensor for selective detection of Zn2+ in aqueous medium," Journal of Molecular Structure, vol. 1264, 2022.
• M. Mary Mathew and A. Sreekanth, "Zn2+ion responsive fluorescent chemosensor probe of Thiophene diocarbohydrazide derivatives," Inorganica Chimica Acta, vol. 516, 2021.
• H. Kim, D. Gil, and C. Kim, "Selective fluorescent detection of Zn 2+ by a rhodanine‐based chemosensor," Journal of the Chinese Chemical Society, vol. 69, no. 5, pp. 856-863, 2022.
• X. Wang, Z. Liu, F. Qian, and W. He, "A bezoimidazole-based highly selective and low-background fluorescent sensor for Zn2+," Inorganic Chemistry Communications, vol. 15, pp. 176-179, 2012.
• C. Quan, J. Liu, W. Sun, and X. Cheng, "Highly sensitive and selective fluorescence chemosensors containing phenanthroline moieties for detection of Zn2+ and Cd2+ ions," Chemical Papers, vol. 74, no. 2, pp. 485-497, 2019.
• Y. Li, R. Song, J. Zhao, Y. Liu, and J. Zhao, "Synthesis, structure, and properties of a novel naphthalene derived fluorescent probe for the detection of Zn2+," Polyhedron, vol. 234, 2023.
• G. Tian, Y.-Z. Han, and Q. Yang, "1, 10-phenanthroline derivative as colorimetric and ratiometric fluorescence probe for Zn2+ and Cd2+," Results in Chemistry, vol. 5, 2023.
• K. Lu et al., "Synthesis of a BINOL-Based C(3) Symmetric Schiff Base and Its Fluorescence Response to Zn(2)," Chempluschem, vol. 88, no. 3, p. e202300036, Mar 2023.
• C. Amoah, C. Obuah, M. K. Ainooson, L. Hamenu, A. Oppong, and A. Muller, "A new sulfonamide-based chemosensor for potential fluorescent detection of Cu2+ and Zn2+ ions," Tetrahedron, vol. 133, 2023.
• S. Y. Park et al., "A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Cd2+ and Zn2+," The Journal of Organic Chemistry, vol. 73, no. 21, pp. 8212-8218, 2008/11/07 2008.
• P. G. Sutariya, H. Soni, S. A. Gandhi, and A. Pandya, "Luminescent behavior of pyrene-allied calix[4]arene for the highly pH-selective recognition and determination of Zn2+, Hg2+ and I−via the CHEF-PET mechanism: computational experiment and paper-based device," New Journal of Chemistry, 10.1039/C9NJ01388A vol. 43, no. 25, pp. 9855-9864, 2019.
• S. Erdemir and B. Tabakci, "Highly sensitive fluorometric detection of Zn2+ ion by calix [4] arene derivative appended 4-biphenylcarbonitrile," Dyes and Pigments, vol. 151, pp. 116-122, 2018.
• S. Ullmann et al., "Zn2+-Ion Sensing by Fluorescent Schiff Base Calix[4]arene Macrocycles," Chemistry – A European Journal, vol. 23, no. 16, pp. 3824-3827, 2017.
• L. Li, L.-t. Du, J. Sun, and C.-g. Yan, "Synthesis, crystal structure of bis-terpyridinyl-calix[4]arene derivatives and fluorescent sensor for Zn2+," Chemical Research in Chinese Universities, vol. 29, no. 5, pp. 874-878, 2013/10/01 2013.
• J. F. Zhang, S. Bhuniya, Y. H. Lee, C. Bae, J. H. Lee, and J. S. Kim, "Novel 2,2′-bipyridine-modified calix[4]arenes: ratiometric fluorescent chemosensors for Zn2+ ion," Tetrahedron Letters, vol. 51, no. 29, pp. 3719-3723, 2010/07/21/ 2010.
• Y.-T. Huang, M. Xue, and Y. Yang, "Imidazobenzimidazole fused azacalix [4]arenes: Synthesis, structure, and Zn2+-selective colorimetric-fluorometric sensor," Chinese Chemical Letters, p. 108294, 2023/03/05/ 2023.
• R. Joseph, J. P. Chinta, and C. P. Rao, "Lower Rim 1,3-Diderivative of Calix[4]arene-Appended Salicylidene Imine (H2L): Experimental and Computational Studies of the Selective Recognition of H2L toward Zn2+ and Sensing Phosphate and Amino Acid by [ZnL]," The Journal of Organic Chemistry, vol. 75, no. 10, pp. 3387-3395, 2010/05/21 2010.
• R. K. Pathak, A. G. Dikundwar, T. N. G. Row, and C. P. Rao, "A lower rim triazole linked calix[4]arene conjugate as a fluorescence switch on sensor for Zn2+ in blood serum milieu," Chemical Communications, 10.1039/C0CC00219D vol. 46, no. 24, pp. 4345-4347, 2010.
• B. Tabakci, H. M. A. Ahmed, and S. Erdemir, "Fast and Reversible “Turn on” Fluorescent Sensors Based on Bisphenol-a for Zn2+ in Aqueous Solution," Journal of Fluorescence, vol. 29, no. 5, pp. 1079-1087, 2019/09/01 2019.
• E. Ozcelik, F. Temel, S. Erdemir, B. Tabakci, and M. Tabakci, "QCM sensors coated with calix [4] arenes bearing sensitive chiral moieties for chiral discrimination of 1-phenylethylamine enantiomers," Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 95, pp. 35-48, 2019.
• X. Mu, L. Shi, L. Yan, and N. Tang, "A 2-Hydroxy-1-naphthaldehyde Schiff Base for Turn-on Fluorescence Detection of Zn(2+) Based on PET Mechanism," J Fluoresc, vol. 31, no. 4, pp. 971-979, Jul 2021.
• J. Zhu et al., "A Schiff base fluorescence probe for highly selective turn-on recognition of Zn2+," Tetrahedron Letters, vol. 58, no. 4, pp. 365-370, 2017.