DOI: https://doi.org/10.14710/jksa.26.8.318-323

In Silico DFT (Density Functional Theory) Study of Chemosensor Selectivity of 3-Oxo-3H-Benzo[f]chromen-2-Carboxylic Acid (ABKK) on Sodium Metal Ion Using FMO (Frontier Molecular Orbital) Analysis

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Sumedang, Indonesia

Received: 13 Oct 2023; Revised: 6 Nov 2023; Accepted: 14 Nov 2023; Published: 15 Nov 2023.
Open Access Copyright 2023 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

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Abstract
The chemosensor selectivity of 3-oxo-3H-benzo[f]chromen-2-carboxylic acid (ABKK) toward Na+ metal ionhas been successfully studied in silico using FMO (Frontier Molecular Orbital) analysis method. The geometry of the ABKK structure was optimized by the DFT (Density Functional Theory) method with a function/basis set: M06/6-31G (d, p). Afterward, the electronic properties of the ABKK structure before and after binding to sodium ion were analyzed and compared with the ABKK+other metal ion structures representing valence charges 1-3 and within the constraints of the basis set used. The results of geometry optimization showed that 1ABKK+Na+ has a more positive frequency/minima than 2ABKK+Na+ with interaction energies of 145 and 200.5 kcal/mol, respectively. Ignoring the role of solvents, FMO analysis revealed that the bandgap energy of fluorophore and receptor interactions (∆E LUMO Fl-Rs 1ABKK+Na+) and (∆E HOMO Fl-Rs 2ABKK+Na+) were 0.631 and 0.336 eV, correspondingly. In addition, the bandgap energy of fluorophore/∆E Fl 1ABKK+Na+ and 2ABKK+Na+ were calculated at 4.347 and 4.362 eV. Comparing those two types of bandgap energies with the bandgap belonging to ABKK+other metal ions, the excitation, and PET (Photoinduced Electron Transfer) processes were estimated to be relatively favorable experienced by 2ABKK+Na+. Finally, the selectivity of ABKK toward sodium metal ions from the computational calculations was relatively in agreement with the laboratory experimental results.
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Keywords: Chemosensor; sodium ion; DFT; FMO; bandgap
Funding: Universitas PadjadjaranIHibah RKDU (1549/UN6.3.1/PT.00/2023); Hibah ALG Prof. Ace T. Hidayat (1549/UN6.3.1/PT.00/2023)

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Section: Research Articles
Language : EN
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  1. Sri Wahyuni, Rimadani Pratiwi, Penggunaan Kemosensor Untuk Mendeteksi Ion Logam, Farmaka, 4, 3, 1-17
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  4. Vinod Kumar Gupta, Naveen Mergu, Lokesh Kumar Kumawat, Ashok Kumar Singh, A reversible fluorescence “off–on–off” sensor for sequential detection of aluminum and acetate/fluoride ions, Talanta, 144, (2015), 80-89 https://doi.org/10.1016/j.talanta.2015.05.053
  5. Naveen Mergu, Ashok Kumar Singh, Vinod Kumar Gupta, Highly Sensitive and Selective Colorimetric and Off-On Fluorescent Reversible Chemosensors for Al3+ Based on the Rhodamine Fluorophore, Sensors, 15, 4, (2015), 9097-9111 https://doi.org/10.3390/s150409097
  6. Vinod Kumar Gupta, Ashok Kumar Singh, Naveen Mergu, Antipyrine based Schiff bases as Turn-on Fluorescent sensors for Al (III) ion, Electrochimica Acta, 117, (2014), 405-412 https://doi.org/10.1016/j.electacta.2013.11.143
  7. Ismail Abdulazeez, Chanbasha Basheer, Abdulaziz A. Al-Saadi, A selective detection approach for copper(ii) ions using a hydrazone-based colorimetric sensor: spectroscopic and DFT study, RSC Advances, 8, 70, (2018), 39983-39991 https://doi.org/10.1039/C8RA08807A
  8. Jamaludin Al Anshori, Daliah Ismalah, Ajar Faflul Abror, Achmad Zainuddin, Ika Wiani Hidayat, Muhammad Yusuf, Rani Maharani, Ace Tatang Hidayat, A new highly selective “off–on” typical chemosensor of Al3+, 1-((Z)-((E)-(3,5-dichloro-2-hydroxybenzylidene)hydrazono)methyl) naphthalene-2-ol, an experimental and in silico study, RSC Advances, 12, 5, (2022), 2972-2979 https://doi.org/10.1039/D1RA08232A
  9. Ruslan Guliyev, Design strategies for chemosensors and their applications in molecular scale logic gates, Bilkent Universitesi (Turkey), 2013
  10. Teresa L. Mako, Joan M. Racicot, Mindy Levine, Supramolecular Luminescent Sensors, Chemical Reviews, 119, 1, (2019), 322-477 https://doi.org/10.1021/acs.chemrev.8b00260
  11. Tasawan Keawwangchai, Nongnit Morakot, Banchob Wanno, Fluorescent sensors based on BODIPY derivatives for aluminium ion recognition: an experimental and theoretical study, Journal of Molecular Modeling, 19, (2013), 1435-1444 https://doi.org/10.1007/s00894-012-1698-3
  12. I. Flaming, Molecular Orbital Theory, in: Molecular Orbitals and Organic Chemical Reactions, John Wiley & Sons, Ltd., 2010, https://doi.org/10.1002/9780470689493.ch1
  13. Jascha Melomedov, Julian Robert Ochsmann, Michael Meister, Frédéric Laquai, Katja Heinze, Tuning Reductive and Oxidative Photoinduced Electron Transfer in Amide-Linked Anthraquinone–Porphyrin–Ferrocene Architectures, European Journal of Inorganic Chemistry, 2014, 11, (2014), 1984-2001 https://doi.org/10.1002/ejic.201400118
  14. Hua Lu, ShuShu Zhang, HanZhuang Liu, YanWei Wang, Zhen Shen, ChunGen Liu, XiaoZeng You, Experimentation and Theoretic Calculation of a BODIPY Sensor Based on Photoinduced Electron Transfer for Ions Detection, The Journal of Physical Chemistry A, 113, 51, (2009), 14081-14086 https://doi.org/10.1021/jp907331q
  15. Bilge Turfan, Engin U. Akkaya, Modulation of Boradiazaindacene Emission by Cation-Mediated Oxidative PET, Organic Letters, 4, 17, (2002), 2857-2859 https://doi.org/10.1021/ol026245t
  16. Selin Manoj Kumar, Dhanapal Jothi, Sathishkumar Munusamy, Saravanan Enbanathan, Sathiyanarayanan Kulathu Iyer, Imidazole-derived new colorimetric/fluorometric chemosensor for the sensitive recognition of CN− ions: Real-time application in food samples and fluorescence bio-imaging, Journal of Photochemistry and Photobiology A: Chemistry, 434, (2023), 114269 https://doi.org/10.1016/j.jphotochem.2022.114269
  17. Venkatesan Muthukumar, Sathiyanarayanan Kulathu Iyer, A simple and optically responsive chemosensor for the detection of Al3+ and Cr3+: In live cells and real sample analysis, Inorganic Chemistry Communications, 122, (2020), 108289 https://doi.org/10.1016/j.inoche.2020.108289
  18. Deblina Sarkar, Ajoy Kumar Pramanik, Tapan Kumar Mondal, Coumarin based fluorescent ‘turn-on’ chemosensor for Zn2+: An experimental and theoretical study, Journal of Luminescence, 146, (2014), 480-485 https://doi.org/10.1016/j.jlumin.2013.09.080
  19. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, in: Gaussian Inc, 2010,
  20. S. F. Boys, F. Bernardi, The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors, Molecular Physics, 19, 4, (1970), 553-566 https://doi.org/10.1080/00268977000101561
  21. Frank Jensen, Introduction to Computational Chemistry, 2nd ed., Wiley, United States, 1999,
  22. Denis Jacquemin, Eric A. Perpète, Ilaria Ciofini, Carlo Adamo, Rosendo Valero, Yan Zhao, Donald G. Truhlar, On the Performances of the M06 Family of Density Functionals for Electronic Excitation Energies, Journal of Chemical Theory and Computation, 6, 7, (2010), 2071-2085 https://doi.org/10.1021/ct100119e
  23. Robert B. Macgregor Jr, Gregorio Weber, Fluorophores in Polar Media: Spectral Effects of The Langevin Distribution of Electrostatic Interactions, Annals of the New York Academy of Sciences, 366, 1, (1981), 140-154 https://doi.org/10.1111/j.1749-6632.1981.tb20751.x

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