Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin
derivative: DFT calculation and practical application in herbal and black tea
samples

KORAN, Kenan; Aydin, Duygu; KARAGOZ, Abdurrahman; YILMAZ, Ibrahim; OZEN, FURKAN; Görgülü, Ahmet Orhan; ARSLAN, FATMA NUR; SAVRAN, TAHIR; KARUK ELMAS, Sukriye Nihan

doi:10.3906/kim-2004-63

Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples

Tahir SAVRAN, (Karamanoğlu Mehmetbey Üniversitesi, Kamil Özdağ Fen Fakültesi, Kimya Bölümü, Karaman, Türkiye)

Abdurrahman KARAGÖZ, (Karamanoğlu Mehmetbey Üniversitesi, Kamil Özdağ Fen Fakültesi, Kimya Bölümü, Karaman, Türkiye)

Şükriye Nihan KARUK ELMAS, (Karamanoğlu Mehmetbey Üniversitesi, Kamil Özdağ Fen Fakültesi, Kimya Bölümü, Karaman, Türkiye)

Duygu AYDIN, (Karamanoğlu Mehmetbey Üniversitesi, Kamil Özdağ Fen Fakültesi, Kimya Bölümü, Karaman, Türkiye)

Furkan ÖZEN, (Akdeniz Üniversitesi, Eğitim Fakültesi, Matematik ve Fen Bilimleri Bölümü, Antalya, Türkiye)

Kenan KORAN, (Fırat Üniversitesi, Fen Fakültesi, Kimya Bölümü, Elazığ, Türkiye)

Fatma Nur ARSLAN, (Karamanoğlu Mehmetbey Üniversitesi, Kamil Özdağ Fen Fakültesi, Kimya Bölümü, Karaman, Türkiye)

Ahmet Orhan GÖRGÜLÜ, (Fırat Üniversitesi, Fen Fakültesi, Kimya Bölümü, Elazığ, Türkiye)

İbrahim YILMAZ (Karamanoğlu Mehmetbey Üniversitesi, Kamil Özdağ Fen Fakültesi, Kimya Bölümü, Karaman, Türkiye)

Turkish Journal of Chemistry

6 0

Yıl: 2020 Cilt: 44 Sayı: 4 Sayfa Aralığı: 1148 - 1163 Metin Dili: İngilizce DOI: 10.3906/kim-2004-63 İndeks Tarihi: 22-06-2022

Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples

Öz:

A fluorogenic probe based on a coumarin-derivative for $Cu^{2+}$ sensing in $CH_3 CN/H_2 O$ media (v/v, 95/5, 5.0 µM) was developed and applied in real samples. 3-(4-chlorophenyl)-6,7-dihydroxy-coumarin (MCPC) probe was obtained by synthetic methodologies and identified by spectral techniques. The probe MCPC showed remarkable changes with a “turn-off” fluorogenic sensing approach for the monitoring of $Cu^{2+}$ at 456 nm under an excitation wavelength of 366 nm. The response time of the probe MCPC was founded as only 1 min. The detection limit of the probe MCPC was recorded to be 1.47 nM. The binding constant and possible stoichiometric ratio (1:1) values were determined by Benesi-Hildebrand and Job’s plot systems, respectively. The mechanism of the probe MCPC with $Cu^{2+}$ was further confirmed by ESI-MS and FT-IR analyses, as well as supported by theoretical calculations. Furthermore, the probe MCPC was successfully employed for the practical applications to sense $Cu^{2+}$ in different herbal and black tea samples. The proposed sensing method was also verified by ICP-OES method.

Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Wang S, Ding H, Wang Y, Fan C, Liu G et al. A colorimetric and ratiometric fluorescent sensor for sequentially detecting $Cu ^{2+}$ and arginine based on a coumarin-rhodamine B derivative and its application for bioimaging. RSC Advances 2019; 9 (12): 6643-6649. doi: 10.1039/c8ra09943j
2. Roy N, Nath S, Dutta A, Mondal P, Paul PC et al. A highly efficient and selective coumarin based fluorescent probe for colorimetric detection of $Fe ^{3+}$ and fluorescence dual sensing of $Zn ^{2+} and Cu ^{2+}$ . RSC Advances 2016;6 (68): 63837-63847. doi: 10.1039/c6ra12217e
3. Bekhradnia A, Domehri E, Khosravi M. Novel coumarin-based fluorescent probe for selective detection of Cu (II). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2016; 152 (1): 18-22. doi: 10.1016/j.saa.2015.07.029
4. Jung HS, Kwon PS, Lee JW, Kim JII, Hong CS et al. Coumarin-derived $Cu ^{2+}$ -selective fluorescence sensor: synthesis, mechanisms, and applications in living cells. Journal of the American Chemical Society 2009; 131 (5): 2008-2012. doi: 10.1021/ja808611d
5. Kim MH, Jang HH, Yi S, Chang SK, Han MS. Coumarin-derivative-based off-on catalytic chemodosimeter for $Cu ^{2+}$ ions. Chemical Communications 2009; 32 (1): 4838-4840. doi: 10.1039/b908638b
6. Shi Y, Wang R, Yuan W, Liu Q, Shi M et al. Easy-to-use colorimetric cyanine probe for the detection of $Cu ^{2+}$ in Wilson’s disease. ACS Applied Materials & Interfaces, 2018; 10 (24): 20377-20386. doi: 10.1021/acsami.8b07081
7. Yeh JT, Chen WC, Liu SR, Wu SP. A coumarin-based sensitive and selective fluorescent sensor for copper(II) ions. New Journal of Chemistry 2014; 38 (9): 4434-4439. doi: 10.1039/c4nj00695j
8. Qian B, Váradi L, Trinchi A, Reichman SM, Bao L et al. The Design and synthesis of fluorescent coumarin derivatives and their study for $Cu ^{2+}$ sensing with an application for aqueous soil extracts. Molecules, 2019; 24 (19): 3569. doi: 10.3390/molecules24193569
9. Arslan FN, Geyik GA, Koran K, Ozen F, Aydin D et al. Fluorescence “turn on-off” sensing of copper (II) ions utilizing coumarin-based chemosensor: experimental study, theoretical calculation, mineral and drinking water analysis. Journal of Fluorescence 2020; 30 (1): 317-327. doi: 10.1007/s10895-020-02503-4
10. Wu X, Wang H, Yang S, Tian H, Liu Y et al. A novel coumarin-based fluorescent probe for sensitive detection of copper(II) in wine. Food Chemistry 2019; 284 (1): 23-27. doi: 10.1016/j.foodchem.2019.01.090
11. Yan F, Bai Z, Chen Y, Zu F, Li X et al. Ratiometric fluorescent detection of copper ıons using coumarinfunctionalized carbon dots based on FRET. Sensors and Actuators B: Chemical 2018; 275 (1): 86-94. doi: 10.1016/j.snb.2018.08.034
12. Karuk Elmas SN, Gunay IB, Koran K, Ozen F, Aydin D et al. An ultrasensitive and selective “turn off” fluorescent sensor with simple operation for the determination of trace copper (II) ions in water and various beverage samples. Supramolecular Chemistry 2019; 31 (12): 756-766. doi: 10.1080/10610278.2019.1702195
13. Aksuner N, Henden E, Yilmaz I, Cukurovali A. A highly sensitive and selective fluorescent sensor for the determination of copper (II) based on a schiff base. Dyes and Pigments 2009; 83 (2): 211-217. doi: 10.1016/j.dyepig.2009.04.012
14. Aksuner N, Henden E, Yilmaz I, Cukurovali A. Selective optical sensing of copper(II) ions based on a novel cyclobutane-substituted schiff base ligand embedded in polymer films. Sensors and Actuators B: Chemical 2008; 134 (2): 510-515. doi: 10.1016/j.snb.2008.05.041
15. Wang Y, Meng Q, Han Q, He G, Hu Y et al. Selective and sensitive detection of cysteine in water and live cells using a coumarin-$Cu ^{2+}$ fluorescent ensemble. New Journal of Chemistry 2018; 42 (19): 15839-15846. doi: 10.1039/c8nj03809k
16. Kumar A, Mondal S, Kayshap KS, Hira SK, Manna PP et al. Water switched aggregation/disaggregation strategies of a coumarin-naphthalene conjugated sensor and its selectivity towards $Cu ^{2+} and Ag^{+}$ ions along with cell ımaging studies on human osteosarcoma cells (U-2 OS). New Journal of Chemistry 2018; 42 (13): 10983-10988. doi: 10.1039/c8nj01631c
17. Zhang J, Zhao B, Li C, Zhu X, Qiao R. A BODIPY-based “turn-on” fluorescent and colorimetric sensor for selective detection of $Cu ^{2+}$ in aqueous media and its application in cell imaging. Sensors and Actuators B: Chemical 2014; 196 (1): 117-122. doi: 10.1016/j.snb.2014.01.116
18. Hormozi-Nezhad MR, Taghipour M. An ultrasensitive and selective turn-off fluorescent nanoprobe for the detection of copper ions. Analytical Methods 2015; 7 (12): 5067-5073. doi: 10.1039/c5ay00766f
19. Joo DH, Mok JS, Bae GH, Oh SE, Kang JH et al. Colorimetric detection of $Cu ^{2+}$ and fluorescent detection of $PO^{3−}_{4} and S 2−$ by a multifunctional chemosensor. Industrial & Engineering Chemistry Research 2017; 56 (30): 8399-8407. doi: 10.1021/acs.iecr.7b01115
20. Guo Z, Hu T, Wang X, Sun T, Li T et al. Highly sensitive and selective fluorescent sensor for visual detection of $Cu ^{2+}$ in water and food samples based on oligothiophene derivative. Journal of Photochemistry and Photobiology A: Chemistry 2019; 371 (1): 50-58. doi: 10.1016/j.jag.2018.07.004
21. Chang Y, Li B, Mei H, Yang L, Xu K et al. Indole-based colori/fluorimetric probe for selective detection of Cu 2+ and application in living cell imaging. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2020; 226 (1): 117631. doi: 10.1016/j.saa.2019.117631
22. Wu SP, Huang ZM, Liu SR, Chung PK. A pyrene-based highly selective turn-on fluorescent sensor for copper(II) ion and its application in live cell imaging. Journal of Fluorescence 2012; 22 (1): 253-259. doi: 10.1007/s10895-011- 0955-7
23. Jiao X, Xiao Z, Hui P, Liu C, Wang Q et al. A highly selective and pH-tolerance fluorescent probe for $Cu ^{2+}$ based on a novel carbazole-rhodamine hybrid dye. Dyes and Pigments 2019; 160 (1): 633-640. doi: 10.1016/j.dyepig.2018.08.060
24. Li J, Ge J, Zhang Z, Qiang J, Wei T et al. A cyanine dye-based fluorescent probe as ındicator of copper clock reaction for tracing Cu 2+ -catalyzed oxidation of cysteine. Sensors and Actuators B: Chemical 2019; 296 (1): 126578. doi: 10.1016/j.snb.2019.05.055
25. Özen F, Tekin S, Koran K, Sandal S, Görgülü AO. Synthesis, structural characterization, and in vitro anticancer activities of new phenylacrylonitrile derivatives. Applied Biological Chemistry 2016; 59 (1): 239-248. doi: 10.1007/s13765-016-0163-x
26. Buu-Hoi NP, Saint-Ruf G, Lobert B. Oxygen heterocycles. part XIV. hydroxylated 3-awl- and 3-pyridyl-coumarins. Journal of the Chemical Society C: Organic 1968; 16 (1): 2069-2070. doi: 10.1039/J39690002069
27. Elgazzar E, Dere A, Özen F, Koran K, Al-Sehemi AG et al. Design and fabrication of dioxyphenylcoumarin substituted cyclotriphosphazene compounds photodiodes. Physica B: Condensed Matter 2017; 515 (1): 8-17. doi: 10.1016/j.physb.2017.03.025
28. Aydin D. A novel turn on fluorescent probe for the determination of Al 3+ and Zn 2+ ions and its cells applications. Talanta 2020; 210 (1): 120615. doi: 10.1016/j.talanta.2019.120615
29. Qiu S, Cui S, Shi F, Pu S. Novel diarylethene-based fluorescent switching for the detection of Al 3+ and construction of logic circuit. ACS Omega 2019; 4 (1): 14841-14848. doi: 10.1021/acsomega.9b01432
30. Karuk Elmas ŞN, Yilmaz I. A turn off-on fluorescent chemosensor for sequential determination of mercury and biothiols. Journal of Fluorescence 2018; 28 (1): 1451-1458. doi: 10.1007/s10895-018-2320-6
31. Karuk Elmas ŞN, Ozen F, Koran K, Görgülü AO, Sadi G et al. Selective and sensitive fluorescent and colorimetric chemosensor for detection of CO2−3 anions in aqueous solution and living cells. Talanta 2018; 188 (1): 614-622. doi: 10.1016/j.talanta.2018.06.036
32. Huang CY. Determination of binding stoichiometry by the continuous variation method: the Job plot. Methods in Enzymol 1982; 87 (1): 509-525. doi: 10.1016/S0076-6879(82)87029-8
33. Frisch AMJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA et al. Gaussian 09 Revision D.01. 2014.
34. Dennington R, Keith TA, Millam JM. GaussView Version 5. 2009.
35. Becke AD. Becke’s three parameter hybrid method using the LYP correlation functional. The Journal of Chemical Physics 1993; 98 (1): 5648-5652. doi: 10.1063/1.464913
36. Lee C, Hill C, Carolina N. Development of the colic-salvetti correlation-energy formula into a functional of the electron density. Physical Review B 1988; 37 (2): 785-789. doi: 10.1103/PhysRevB.37.785
37. Hay PJ, Wadt WR. Ab initio effective core potentials for molecular calculations. potentials for the transition metal atoms Sc to Hg. The Journal of Chemical Physics 1985; 82 (1): 270-283. doi: 10.1063/1.448799
38. Yang S, Yin B, Xu L, Gao B, Sun H et al. A natural quercetin-based fluorescent sensor for highly sensitive and selective detection of copper ions. Analytical Methods 2015; 7 (1): 4546-4551. doi: 10.1039/C5AY00375J
39. Duarte LGTA, Coelho FL, Germino JC, Costa GG, Berbigier JF et al. A selective proton transfer optical sensor for copper II based on chelation enhancement quenching effect (CHEQ). Dyes and Pigments 2020; 108566. doi: 10.1016/j.dyepig.2020.108566 40. Hildebrand JH, Benesi HA. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of the American Chemical Society 1949; 71 (8): 2703-2707. doi: 10.1038/164963b0
40. Duan YW, Tang HY, Guo Y, Song ZK, Peng MJ et al. The synthesis and study of the fluorescent probe for sensing $Cu ^{2+}$ 4 based on a novel coumarin Schiff-base. Chinese Chemistry Letters 2014; 25 (7): 1082-1086. doi: 10.1016/j.cclet.2014.05.001
41. Zhou Z, Li N, Tong A. A new coumarin-based fluorescence turn-on chemodosimeter for Cu $Cu ^{2+}$ in water. Analytica Chimica Acta 2011; 702: 81-86. doi: 10.1016/j.aca.2011.06.041

APA	SAVRAN T, KARAGOZ A, KARUK ELMAS S, Aydin D, OZEN F, KORAN K, ARSLAN F, Görgülü A, YILMAZ I (2020). Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. , 1148 - 1163. 10.3906/kim-2004-63
Chicago	SAVRAN TAHIR,KARAGOZ Abdurrahman,KARUK ELMAS Sukriye Nihan,Aydin Duygu,OZEN FURKAN,KORAN Kenan,ARSLAN FATMA NUR,Görgülü Ahmet Orhan,YILMAZ Ibrahim Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. (2020): 1148 - 1163. 10.3906/kim-2004-63
MLA	SAVRAN TAHIR,KARAGOZ Abdurrahman,KARUK ELMAS Sukriye Nihan,Aydin Duygu,OZEN FURKAN,KORAN Kenan,ARSLAN FATMA NUR,Görgülü Ahmet Orhan,YILMAZ Ibrahim Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. , 2020, ss.1148 - 1163. 10.3906/kim-2004-63
AMA	SAVRAN T,KARAGOZ A,KARUK ELMAS S,Aydin D,OZEN F,KORAN K,ARSLAN F,Görgülü A,YILMAZ I Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. . 2020; 1148 - 1163. 10.3906/kim-2004-63
Vancouver	SAVRAN T,KARAGOZ A,KARUK ELMAS S,Aydin D,OZEN F,KORAN K,ARSLAN F,Görgülü A,YILMAZ I Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. . 2020; 1148 - 1163. 10.3906/kim-2004-63
IEEE	SAVRAN T,KARAGOZ A,KARUK ELMAS S,Aydin D,OZEN F,KORAN K,ARSLAN F,Görgülü A,YILMAZ I "Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples." , ss.1148 - 1163, 2020. 10.3906/kim-2004-63
ISNAD	SAVRAN, TAHIR vd. "Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples". (2020), 1148-1163. https://doi.org/10.3906/kim-2004-63

APA	SAVRAN T, KARAGOZ A, KARUK ELMAS S, Aydin D, OZEN F, KORAN K, ARSLAN F, Görgülü A, YILMAZ I (2020). Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. Turkish Journal of Chemistry, 44(4), 1148 - 1163. 10.3906/kim-2004-63
Chicago	SAVRAN TAHIR,KARAGOZ Abdurrahman,KARUK ELMAS Sukriye Nihan,Aydin Duygu,OZEN FURKAN,KORAN Kenan,ARSLAN FATMA NUR,Görgülü Ahmet Orhan,YILMAZ Ibrahim Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. Turkish Journal of Chemistry 44, no.4 (2020): 1148 - 1163. 10.3906/kim-2004-63
MLA	SAVRAN TAHIR,KARAGOZ Abdurrahman,KARUK ELMAS Sukriye Nihan,Aydin Duygu,OZEN FURKAN,KORAN Kenan,ARSLAN FATMA NUR,Görgülü Ahmet Orhan,YILMAZ Ibrahim Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. Turkish Journal of Chemistry, vol.44, no.4, 2020, ss.1148 - 1163. 10.3906/kim-2004-63
AMA	SAVRAN T,KARAGOZ A,KARUK ELMAS S,Aydin D,OZEN F,KORAN K,ARSLAN F,Görgülü A,YILMAZ I Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. Turkish Journal of Chemistry. 2020; 44(4): 1148 - 1163. 10.3906/kim-2004-63
Vancouver	SAVRAN T,KARAGOZ A,KARUK ELMAS S,Aydin D,OZEN F,KORAN K,ARSLAN F,Görgülü A,YILMAZ I Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples. Turkish Journal of Chemistry. 2020; 44(4): 1148 - 1163. 10.3906/kim-2004-63
IEEE	SAVRAN T,KARAGOZ A,KARUK ELMAS S,Aydin D,OZEN F,KORAN K,ARSLAN F,Görgülü A,YILMAZ I "Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples." Turkish Journal of Chemistry, 44, ss.1148 - 1163, 2020. 10.3906/kim-2004-63
ISNAD	SAVRAN, TAHIR vd. "Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples". Turkish Journal of Chemistry 44/4 (2020), 1148-1163. https://doi.org/10.3906/kim-2004-63