COMPUTATIONAL INVESTIGATION OF IMIDAZOLIUM IONIC LIQUIDS AND THEIR INTERACTIONS WITH CERTAIN BIO-SPECIES USING DENSITY FUNCTIONAL THEORY
Keywords:
Imidazolium, Ionic Liquids, Dopamine, Ascorbic Acid, Uric Acid, Density Functional Theory (DFT), Interaction Energy, Global Reactivity Descriptors, Bioanalyte DetectionAbstract
Ionic liquids, particularly imidazolium-based variants, have gained significant attention due to their unique properties, such as tunable polarity, high thermal stability, and potential applications in electrochemical devices and biosensing. A detailed computational analysis of imidazolium-based ionic liquids (ILs) and their interactions with biologically significant molecules—dopamine, ascorbic acid, and uric acid—was conducted. Using Density Functional Theory (DFT) with the 6-311++G(d,p) basis set, the electronic properties, molecular structures, and interaction energies of three ILs—EMI-SCN, EMI-DCA, and BMI-PF6—were explored. Structural optimization, HOMO-LUMO gap analysis, and molecular electrostatic potential mapping were employed to uncover binding characteristics and reactivity of the ILs toward the biomolecules. Among the tested ILs, EMI-SCN exhibited the highest interaction energies with all analytes, particularly showing strong affinity for ascorbic acid, indicating its potential in electrochemical sensors. The calculated global reactivity descriptors support the stability and reactivity trends, with EMI-SCN demonstrating superior electronic and electrostatic interactions compared to EMI-DCA and BMI-PF6. EMI-SCN’s unique interaction profiles suggest its suitability for selective detection of dopamine, ascorbic acid, and uric acid in biological environments. These findings pave the way for the rational design of ionic liquids aimed at enhancing the performance of biosensors and electrochemical devices, offering improved sensitivity and selectivity for biological molecule detection.
References
I. Shukla, M. K., Tiwari, H., Verma, R., Dong, W. L., Azizov, S.,Kumar, B.Kumar, D. (2023). Role and recent advancements of ionic liquids in drug delivery systems. Pharmaceutics, 15(2), 702.
II. Bolton EE, Wang Y, Thiessen PA, et al. PubChem: Integrated Platform of Small Molecules and Biological Activities. In: Annual Reports in Computational Chemistry. 2008. p. 217–41.
III. O’Boyle NM, Banck M, James CA, et al. Open babel: an open chemical toolbox. J Chem Informatics. 2011;3:33.
IV. Frisch MJ, Trucks GW, Schlegel HB, et al. GAUSSIAN 09 (revision A.2). Wallingford, CT: Gaussian, Inc. D J Gaussian 09. 1998. B.01.
V. Sangeetha KG, Aravindakshan KK, Safna Hussan KP, Insight into the theoretical and experimental studies of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone N(4)-methyl-N(4)- phenylthiosemicarbazone – a potential NLO material. J Mol Struct. 2017;1150:135–145.
VI. Safna Hussan K. P, Abdul Rahoof K. A, Zubair Medammal, M. Shahin Thayyil & Thekkekara D. Babu (2022): Theoretical insights into the radical scavenging activity of glipizide: DFT and molecular docking studies, Free Radical Research, 2022, 53-62.
VII. Abdul Rahoof K.A, M.C Fathima Naja, Mohamed Shahin Thayyil (2024). Toxicity Prediction of Imidazolium and Pyridinium Ionic Liquids: A DFT-Based Approach, International Educational Journal of Science and Engineering (IEJSE), Vol: 7, Issue: 8, 18-23
VIII. Kar R, Chandrakumar KRS, Pal S. The influence of electric field on the global and local reactivity descriptors: Reactivity and stability of weakly bonded complexes. J Phys Chem A. 2007;111(2):375–383.
IX. Jian-De Xie, Chueh-Han Wang, Jagabandhu Patra, Purna Chandra Rath, Yasser Ashraf Gandomi , Quanfeng Dong and Jeng-Kuei Chang. Ionic liquids with various constituent ions to optimize non enzymatic electrochemical detection properties of graphene electrodes. ACS Sustainable Chem.Eng 2019.
X. J. Sponer, P. Hobza and J. Leszczynski. Computational approaches to the studies of the interactions of nucleic acid bases. Theoretical Computational Chemistry, Vol.8, Elsevier,1999.
XI. Sai Saravanan Ambi Venkataramanan and Ramalingam Anantharaj. DFT Study on interaction of estrone and imidazolium-based hydrophobic ionic liquids, IntechOpen 2020.
XII. V. V. Singh, A. K. Nigam, A. Batra, M. Boopathi, B. Singh, and R. Vijayaraghavan, “Applications of Ionic Liquids in Electrochemical Sensors and Biosensors,” Int. J. Electrochem., vol. 2012, no. Figure 1, pp. 1–19, 2012, doi: 10.1155/2012/165683.
XIII. 6. D. S. Silvester, “Recent advances in the use of ionic liquids for electrochemical sensing,” Analyst, vol. 136, no. 23, pp. 4871–4882, 2011, doi: 10.1039/c1an15699c.
XIV. D. Weingarth et al., “Electrochemical Stability of Imidazolium Based Ionic Liquids Containing Cyano Groups in the Anion: A Cyclic Voltammetry, XPS and DFT Study,” J. Electrochem. Soc., vol. 159, no. 7, pp. H611–H615, 2012, doi: 10.1149/2.001207jes.
XV. A. Paul, S. Muthukumar, and S. Prasad, “Review—Room-Temperature Ionic Liquids for Electrochemical Application with Special Focus on Gas Sensors,” J. Electrochem. Soc., vol. 167, no. 3, p. 037511, 2020, doi: 10.1149/2.0112003jes.
XVI. Kianfar, E., Mafi, S. (2021). Ionic liquids: properties, application, and synthesis. Fine Chemical Engineering, 21-29.
XVII. Gonçalves, A. R., Paredes, X., Cristino, A. F., Santos, F. J. V., Queirós,
XVIII. C. S. (2021). Ionic liquids—A review of their toxicity to living organisms. International Journal of Molecular Sciences, 22(11), 5612.
XIX. Nu’aim, M. N., Bustam, M. A. (2018, April). Toxicity prediction of ionic liquids based on Daphnia magna by using density functional theory. In IOP Conference Series: Materials Science and Engineering (Vol. 344, No. 1, p. 012017). IOP Publishing.
XX. Yuriy O Andriyko, Wolfgang Reischl, and Gerhard E Nauer. Trialkyl-substituted imidazolium-based ionic liquids for electrochemical applications: basic physicochemical properties. Journal of Chemical & Engineering Data, 54(3):855–860, 2009.
XXI. Robert Biczak, Barbara Pawlowska, Piotr Ba-lczewski, and Piotr Rychter. The role of the anion in the toxicity of imidazolium ionic liquids. Journal of hazardous materials, 274:181–190, 2014.
XXII. David J Couling, Randall J Bernot, Kathryn M Docherty, JaNeille K Dixon, and Edward J Mag- inn. Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling. Green Chemistry, 8(1):82–90, 2006.
XXIII. Kathryn M Docherty, Michelle V Joyce, Konrad J Kulacki, and Charles F Kulpa. Microbial biodegra- dation and metabolite toxicity of three pyridinium-based cation ionic liquids. Green Chemistry, 12(4):701–712, 2010.
XXIV. Maylis Orio, Dimitrios A Pantazis, and Frank Neese. Density functional theory. Photosynthesis research, 102:443–453, 2009.
XXV. S´onia N Pedro, Carmen SR Freire, Armando JD Silvestre, and Mara G Freire. Ionic liquids in drug delivery. Encyclopedia, 1(2):324–339, 2021.
XXVI. Eduardo Perales, Laura Lomba, Mar´ıa Garc´ıa-Escudero, Esther Sarasa, Carlos E Lafuente, and Beatriz Giner. Toxicological study of some ionic liquids. Green Processing and Synthesis, 7(4):287– 295, 2018.
XXVII. A Romero, A Santos, J Tojo, and AJJOHM Rodr´ıguez. Toxicity and biodegradability of imidazolium ionic liquids. Journal of hazardous materials, 151(1):268–273, 2008.
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