Abstract
A new thiosemicarbazide-naphthalene-based fluorescent chemosensor FNC ((2-(furan-2-carbonyl)-N-(naphthalen-1-yl)hydrazine-1-carbothioamide)) for Zn2+ was synthesized and identified. FNC was applied to selectively detect Zn2+ with fluorescent turn-on response. The detection limit was determined to be 1.93 µM, which is much below the WHO standard (76.5 µM). The detecting mechanism of FNC to Zn2+ was revealed to bind FNC to Zn2+ in the proportion of 1: 1 by Job plot, ESI-mass and 1H NMR titrations. DFT and TD-DFT calculations were performed for FNC and FNC-Zn2+, which provide insight into structural, electronic and photophysical properties.
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J. Briffa, E. Sinagra and R. Blundell, Heliyon, 6, e04691 (2020).
M. Ariannezhad, D. Habibi, S. Heydari and V. Khorramabadi, Korean J. Chem. Eng., 38, 1510 (2021).
M. Theetharappan and M. A. Neelakantan, J. Fluoresc., 31, 1277 (2021).
P. Cheng, Y. Ren, L. Yang, R. Li, X. Wang, B. Li and H. Yuan, Korean J. Chem. Eng., 39, 3350 (2022).
Z. Long, Y. Huang, W. Zhang, Z. Shi, D. Yu, Y. Chen, C. Liu and R. Wang, Environ. Monit. Assess., 193 (2021).
J. M. Jung, C. Kim and R. G. Harrison, Sens. Actuators B Chem., 255, 2756 (2018).
A. Pandith, N. Uddin, C. H. Choi and H. S. Kim, Sens. Actuators B Chem., 247, 840 (2017).
H. Xu, C. Zhu, Y. Chen, Y. Bai, Z. Han, S. Yao, Y. Jiao, H. Yuan, W. He and Z. Guo, Chem. Sci., 11, 11037 (2020).
D. Maity and T. Govindaraju, Chem. Commun., 48, 1039 (2012).
D. Choe and C. Kim, J. Chem. Sci., 133 (2021).
X. Wu, Z. Zhang, H. Liu and S. Pu, RSC Adv., 10, 15547 (2020).
D. Xiang, S. Zhang, Y. Wang, K. Sun and H. Xu, Tetrahedron, 106–107, 132648 (2022).
B. Suh, D. Gil, S. Yoon, K.-T. Kim and C. Kim, Chemosensors, 10, 32 (2022).
Y. P. Zhang, W. Y. Niu, C. M. Ma, Y. S. Yang, H. C. Guo and J. J. Xue, Inorg. Chem. Commun., 130, 108735 (2021).
M. Mary Mathew and A. Sreekanth, Inorg. Chim. Acta, 516, 120149 (2021).
J. B. Chae, D. Yun, S. Kim, H. Lee, M. Kim, M. H. Lim, K. T. Kim and C. Kim, Spectrochim. Acta A Mol. Biomol. Spectrosc., 219, 74 (2019).
M. Kiani, M. Bagherzadeh, S. Meghdadi, N. Rabiee, A. Abbasi, K. Schenk-Joß, M. Tahriri, L. Tayebi and T. J. Webster, New J. Chem., 44, 11841 (2020).
M. Ruz, F. Carrasco, P. Rojas, K. Basfi-fer, M. C. Hernández and A. Pérez, Biol. Trace Elem. Res., 188, 177 (2019).
J. Y. Yun, T. G. Jo, J. Han, H. J. Jang, M. H. Lim and C. Kim, Sens. Actuators B Chem., 255, 3108 (2018).
J. H. Kang and C. Kim, Photochem. Photobiol. Sci., 17, 442 (2018).
M.K. Swami and P.K. Gupta, Proc. Natl. Acad. Sci. India Sect. A - Phys. Sci., 88, 453 (2018).
N. A. S. Pungut, H. Mat Saad, K. S. Sim and K. W. Tan, J. Photochem. Photobiol. A Chem., 414, 113290 (2021).
S. Anbu, A. Paul, K. Surendranath, N. S. Solaiman and A. J. L. Pombeiro, Sens. Actuators B Chem., 337, 129785 (2021).
P. Bhalla, A. Goel, N. Tomer and R. Malhotra, Inorg. Chem. Commun., 136 (2022).
M. X. Lv, L. Y. Bian, W. N. Wu, Z. H. Xu, Y. Wang, X. L. Zhao, Z. Q. Xu, Y. C. Fan and L. L. Yan, Color. Technol., 1 (2021).
N. A. S. Pungut, M. P. Heng, H. M. Saad, K. S. Sim, V. S. Lee and K. W. Tan, J. Mol. Struct., 1238, 130453 (2021).
D. Y. Lee, N. Singh and D. O. Jang, Tetrahedron Lett., 51, 1103 (2010).
C. K. Maurya, U. Pathak and P. K. Gupta, Anal. Bioanal. Chem., 413, 4501 (2021).
Y. Liu, X. Wang, E. Feng, C. Fan and S. Pu, Spectrochim. Acta A Mol. Biomol. Spectrosc., 246, 119052 (2021).
M. S. Kim, D. Yun, J.B. Chae, H. So, H. Lee, K. Kim, M. Kim, M. H. Lim and C. Kim, Sensors, 19, 5458 (2019).
S. Jana, S. Prajapati, K. K. Suryavanshi, S. Goswami, R. Parida and S. Giri, J. Phys. Org. Chem., 33, 1 (2020).
Q. Lin, Y. Q. Fan, P. P. Mao, L. Liu, J. Liu, Y.M. Zhang, H. Yao and T. B. Wei, Chem. A Eur. J., 24, 777 (2018).
J. M. Jung, J. H. Kang, J. Han, H. Lee, M. H. Lim, K. T. Kim and C. Kim, Sens. Actuators B Chem., 267, 58 (2018).
J. H. Kang, J. Han, H. Lee, M. H. Lim, K. T. Kim and C. Kim, Dyes Pigm., 152, 131 (2018).
J. B. Chae, H. Lee and C. Kim, J. Fluoresc., 30, 347 (2020).
J. Sun, T. Li, C. Liu, J. Xue, L. Tian, K. Liu, S. Li and Z. Yang, J. Photochem. Photobiol. A Chem., 406, 113007 (2021).
H. Taş, J. Adams, J. C. Namyslo and A. Schmidt, RSC Adv., 11, 36450 (2021).
N. Mudi, P. Hazra, M. Shyamal, S. Maity, P. K. Giri, S. S. Samanta, D. Mandal and A. Misra, J. Fluoresc., 31, 315 (2021).
H. So, H. Cho, H. Lee, M. C. Tran, K. T. Kim and C. Kim, Microchem. J., 155, 104788 (2020).
F. P. Ying, H. S. Lu, X. Q. Yi, Y. Q. Xu and Y. Y. Lv, Sens. Actuators B Chem., 340 (2021).
N. S. Mohamad, N. H. Zakaria, N. Daud, L. L. Tan, G. C. Ta, L. Y. Heng and N. I. Hassan, Sensors (Switzerland), 21, 1 (2021).
S. C. Lee, M. Lee, B. Suh, J. Lee and C. Kim, ChemistrySelect, 6, 8397 (2021).
B. K. Rani and S. A. John, J. Photochem. Photobiol. A Chem., 418, 113372 (2021).
M. Wu, D. D. Yang, H. W. Zheng, Q. F. Liang, J. Bin Li, Y. Kang, S. Li, C. Jiao, X. J. Zheng and L. P. Jin, Dalton Trans., 50, 1507 (2021).
A. K. K. Bhasin, P. Chauhan and S. Chaudhary, Sens. Actuators B Chem., 330, 129328 (2021).
C. Jiang, L. Yang, P. Li, Y. Liu, S. Li, Y. Fu and F. Ye, Spectrochim. Acta A Mol. Biomol. Spectrosc., 263, 120168 (2021).
S. Jiang, S. Chen, Z. Wang, H. Guo and F. Yang, Sens. Actuators B Chem., 308, 127734 (2020).
E. Bahojb Noruzi, M. Kheirkhahi, B. Shaabani, S. Geremia, N. Hickey, F. Asaro, P. Nitti and H. S. Kafil, Front. Chem., 7 (2019).
K. H. Alharbi, Crit. Rev. Anal. Chem., 1 (2022).
Z. Gao, S. Qiu, M. Yan, H. Liu, S. Lu, H. Lian, P. Zhang, J. Zhu and M. Jin, J. Mol. Struct., 1254, 132312 (2022).
A. Jayaraj, M. S. Gayathri, G. Sivaraman and C. A. S. P, J. Photochem. Photobiol. B Biol., 226, 112371 (2022).
S. Paul and P. Banerjee, Sens. Actuators B Chem., 329, 129172 (2021).
Gaussian 16, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery Jr., J. E. P., F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman and D. J. Fox, Gaussian, Inc., Wallingford CT (2016).
A. D. Becke, J. Chem. Phys., 98, 5648 (1993).
M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople, J. Chem. Phys., 77, 3654 (1982).
P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 28, 213 (1973).
P. J. Hay and W. R. Wadt, J Chem. Phys., 82, 299 (1985).
A. Klamt, C. Moya and J. Palomar, J. Chem. Theory Comput., 11, 4220 (2015).
A. M. Brouwer, Pure Appl. Chem., 83, 2213 (2011).
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The National Research Foundation of Korea (2018R1A2B6001686) is gratefully acknowledged.
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Lee, M., Moon, S., Gil, D. et al. A novel fluorescent turn-on probe based on thiosemicarbazide-naphthalene for selectively detecting Zn2+. Korean J. Chem. Eng. 40, 2010–2016 (2023). https://doi.org/10.1007/s11814-023-1464-5
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DOI: https://doi.org/10.1007/s11814-023-1464-5