Abstract
Utilizing a high-dilution condition method, a new aza-oxo macrocycle, referred to as L, was synthesized as a chemosensor. The chemosensing capabilities of L were thoroughly investigated using fluorescence studies. The obtained results demonstrate that L effectively responds to the presence of zinc ions, leading to a significant increase in fluorescence intensity. Comparative studies were conducted to investigate the impact of various metal cations, including Cr(III), Mn(II), Fe(II), Fe(III), Co(II), Ni(II), Cu(I), Cu(II), Zn(II), Cd(II), Gd(III), Na(I), K(I), Ba(II), Mg(II), Al(III), Pb(II), Sn(II), Hg(II), and Ag(I), on the fluorescence of L in an aqueous ethanol environment. During our investigations, a binding constant value of 7.81 × 105 M−1, with a 1:1 stoichiometry for Zn2+–L interactions, was established. Additionally, a low detection limit of 2.51 × 10−8 M and a rapid response time were observed. Furthermore, the chemical inputs of Zn2+ and Cu2+ ions meet the conditions of an INHIBIT molecular logic gate.
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References
Frederickson, C.J., Koh, J.-Y., Bush, A.I.: Nat. Rev. Neurosci. 6, 449 (2005)
Bush, A.I., Pettingell, W.H., Multhaup, G., Paradis, M., Vonsattel, J.-P., Gusella, J.F., Beyreuther, K., Masters, C.L., Tanzi, R.E.: Science 265, 1464 (1994)
Piskacek, M., Zotova, L., Gábor, Z.: J. Cell. Mol. Med. 13, 693–697 (2009)
Kaur, K., Bhardwaj, V.K., Kaur, N., Singh, N.: Inorg. Chem. Commun. 26, 31–36 (2012)
Gupta, V.K., Sethi, B., Sharma, R.A., Agarwal, S., Bharti, A.: J. Mol. Liq. 177, 114–118 (2013)
Gupta, V.K., Karimi-Maleh, H., Sadegh, R.: Int. J. Electrochem. Sci. 10, 303–316 (2015)
Rout, K., Manna, A.K., Sahu, M., Patra, G.K.: Inorg. Chim. Acta 486, 733–741 (2019)
Kim, M.S., GeunJo, T., Yang, M., Han, J., Lim, M.H., Kim, C.: Spectrochim. Acta A Mol. Biomol Spectrosc. 211, 34–43 (2019)
Kim, A., Lee, H., Yun, D., Jung, U., Kim, K.-T., Kim, C.: Spectrochim. Acta. A Mol. Biomol. Spectrosc. 241, 118652 (2020)
So, H., Choa, H., Lee, H., Tran, M.C., Kim, K.-T., Kim, C.: Microchem. J. 155, 104788 (2020)
Maity, D., Mandal, S.K., Guha, B., Roy, P.: Inorg. Chim. Acta 519, 120258 (2021)
Fu, H., Liu, H., Zhao, L., Xiao, B., Fan, T., Jiang, Y.: Tetrahedron 75, 130710 (2019)
Jonaghani, M.Z., Zali-Boeini, H., Moradi, H.: Spectrochim. Acta. A Mol. Biomol. Spectrosc. 207, 16–22 (2019)
Wang, P., Wu, X., Wu, J.: J. Photochem. Photobiol. A Chem. 382, 111929 (2019)
Rani, B.K., John, S.A.: J. Photochem. Photobiol. A Chem. 418, 113372 (2021)
Wang, P., Xue, S.: X, Yang. Microchem. J. 158, 105147 (2020)
Hu, J.-H., Li, J.-B., Qi, J., Sun, Y.: Sens. Actuators B 208, 581–587 (2015)
Khatun, M., Mandal, J., Tamang, V.W., Ghosh Chowdhury, S., Karmakar, P., Saha, A.: J. Photochem. Photobiol. A Chem. 447, 115231 (2024)
Bumagina, N.A., Antina, E.V., Nikonova, A.Y., Berezin, M.B., Ksenofontov, A.A., Vyugin, A.I.: J. Fluoresc. 26, 1967–1974 (2016)
Yun, J.Y., Chae, J.B., Kim, M., Lim, M.H., Kim, C.: Photochem. Photobiol. Sci. 18, 166–176 (2019)
Mandal, J., Jana, N.C., Chowdhury, S.G., Karmakar, P., Saha, A.: Inorg. Chem. Commun. 156, 111217 (2023)
Behura, R., Dash, P.P., Mohanty, P., Behera, S., Mohanty, M., Dinda, R., Behera, S.K., Barick, A.K., Jali, B.R.: J. Mol. Struct. 1264, 133310 (2022)
Azadbakht, R., Hakimi, M., Khanabadi, J.: Spectrochim. Acta A 250, 119236–119241 (2021)
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J.: GAUSSIAN 09, Revision D.01. Gaussian Inc, Wallingford (2009)
Becke, A.D.: J. Chem. Phys. 98, 5648–5652 (1993)
Lee, C., Yang, W., Parr, R.G.: Phys. Rev. B 37, 785–789 (1988)
Hay, P.J., Wadt, W.R.: J. Chem. Phys. 82, 270–283 (1985)
Wadt, W.R., Hay, P.J.: J. Chem. Phys. 82, 284–298 (1985)
Hay, P.J., Wadt, W.R.: J. Chem. Phys. 82, 299–310 (1985)
Barone, V., Cossi, M.: J. Phys. Chem. A 102, 1995–2001 (1998)
Cossi, M., Barone, V.: J. Chem. Phys. 115, 4708–4717 (2001)
Cossi, M., Rega, N., Scalmani, G., Barone, V.: J. Comput. Chem. 24, 669–681 (2003)
O’Boyle, N.M., Tenderholt, A.L., Langner, K.M.: J. Comput. Chem. 29, 839–845 (2008)
Mondal, P., Sarkar, R., Hens, A., Rajak, K.K.: RSC Adv. 4, 38769–38782 (2014)
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The authors thankfully acknowledge the Faculty of Chemistry of Bu-Ali Sina University and Ministry of Science Research and Technology of Iran.
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Reza Azadbakht and Mostafa Koolivand contributed to the collection of emission spectra, data analysis, and writing the original draft. Hasti Moshiri played a key role in synthesizing the compounds.
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Azadbakht, R., Moshiri, H. & Koolivand, M. Development of a highly selective and sensitive fluorescent chemosensory for zinc ion detection in aqueous ethanol solution: synthesis of a new aza-oxo macrocycle using high-dilution condition method. J Incl Phenom Macrocycl Chem (2024). https://doi.org/10.1007/s10847-024-01223-7
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DOI: https://doi.org/10.1007/s10847-024-01223-7