Energy Band Gap Investigation using First Principle Simulation and Tauc Plot Method of Calixarene and Calixarene-Drug Inclusion Complexes
DOI:
https://doi.org/10.37134/jsml.vol11.sp.8.2023Keywords:
Band gap, Calixarene, DFT, PABA, Quantum Espresso, Tauc relation, UV-VisibleAbstract
Calixarene has attract attention especially in drug delivery and drug sensor systems due to its peculiar properties, such as functional diversity of the upper and lower rims, hydrophobic cavity, chemical stability, zero toxicity, and controlled release profile. These properties make this supramolecule an ideal candidate for drug encapsulation and sensors. P-aminobenzoic acid (PABA) is a drug in sunscreen which is widely used as a ultraviolet (UV) filter and sunburn protector to protect against solar rays. The calix[n]arene (n=4,6,8) and the host-guest interaction of calix[n]-PABA were characterized using UV–visible spectroscopy and the first-principles pseudopotential method, based on the density functional theory (DFT) and the plane-wave method as implemented into Quantum Espresso code. The DFT calculation is performed to find the estimated calix[n]arene and calix[n]arene-drug band gap. The band gap calculated using DFT has usually underestimated the insulating materials for about 30 – 50% of the experimental gap values, depending on the selected type of exchange-correlation chosen. The optical band gap value of calix[n]arene and calix[n]-PABA obtained from the UV-Visible absorption spectrum estimated using the Tauc plot are then compared with the band gap computed by DFT. The band gap narrowing shown by the complexes indicates that calix[n]arene and PABA reacted. Besides, calix[8]arene is the most promising host in this study since the calix[8]-PABA complex has the most significant binding energy. The band gaps and binding energy results will become a reference for future research in calixarene and calixarene-drug material.
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Athar M, Ranjan P, Jha PC. (2018). Investigation of calixarene complexes with dasatinib and lapatinib: A Density Functional Theory approach. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 84, 160-165.
Ayoubi-Chianeh M, Kassaee MZ. (2020). Detection of bendamustine anti-cancer drug via AlN and Si-doped C nanocone and nanosheet sensors by DFT. Structural Chemistry, 31(5), 2041-2050.
Bagus PS, Nelin CJ, Zhao X, Levchenko SV, Davis E, Weng X, Späth F, Papp C, Kuhlenbeck H, Freund HJ. (2019). Revisiting surface core-level shifts for ionic compounds. Physical Review B, 100(11), 1-5.
Borlido P, Schmidt J, Huran AW, Tran F, Marques MAL. (2020). Exchange-correlation functionals for band gaps of solids: benchmark, reparametrization and machine learning. Npj Computational Materials, 6(1), 1-17.
Bredas JL. (2014). Mind the gap! Materials Horizons, 1(1), 17-19.
Chan CTL, Ma C, Chan RCT, Ou HM, Xie HX, Wong AKW, Wang ML, Kwok WM. (2020). A long lasting sunscreen controversy of 4-aminobenzoic acid and 4-dimethylaminobenzaldehyde derivatives resolved by ultrafast spectroscopy combined with density functional theoretical study. Physical Chemistry Chemical Physics, 22(15), 8006-8020.
Edwards NY, Schnable DM, Gearba-dolocan IR, Strubhar JL. (2021). Terpyridine-Functionalized Calixarenes: Synthesis, Characterization and Anion Sensing Applications. Molecules, 26, 87.
Español ES, Villamil MM. (2019). Calixarenes: Generalities and their role in improving the solubility, biocompatibility, stability, bioavailability, detection, and transport of biomolecules. Biomolecules, 9(3), 90.
Fahmy SA, Ponte F, Fawzy IM, Sicilia E, Bakowsky U, Azzazy HMES. (2020). Host-guest complexation of oxaliplatin and para-sulfonatocalix[n]arenes for potential use in cancer therapy. Molecules, 25(24), 5926.
Fort EH, Scott LT. (2016). Selective Recognition of Neutral Guests in an Aqueous Medium by a Biomimetic Calix[6]cryptamide Receptor. Organic and Biomolecular Chemistry, 14(30), 738-746.
García ÁM, Valero R, Illas F. (2017). An Empirical, Yet Practical Way to Predict the Band Gap in Solids by Using Density Functional Band Structure Calculations An empirical , yet practical way to predict the band gap in solids by using density functional band structure calculations. Journal of Physical Chemistry C, 121, 18862-18866.
Gassoumi B, Ghalla H, Chaabane RB. (2019). DFT and TD-DFT investigation of calix[4]arene interactions with TFSI-ion. Heliyon, 5(11), e02822.
Giannozzi P, Baroni S, Bonini N, Calandra M, Car R, Cavazzoni C, Ceresoli D, Chiarotti GL, Cococcioni M, Dabo I, Dal Corso A, De Gironcoli S, Fabris S, Fratesi G, Gebauer R, Gerstmann U, Gougoussis C, Kokalj A, Lazzeri M, Wentzcovitch RM. (2009). Quantum Espresso: A modular and open-source software project for quantum simulations of materials. Journal of Physics Condensed Matter, 21(39), 1-19.
Guan LL, Lim HW, Mohammad TF. (2021). A Review of Current Literature Sunscreens and Photoaging : A Review of Current Literature. American Journal of Clinical Dermatology, 22, 819-828.
Han C, Yang H, Li B, Wang Z. (2020). Exogenous pyruvate facilitates ultraviolet B-induced DNA damage repair by promoting H3K9 acetylation in keratinocytes and melanocytes. Biomedicine and Pharmacotherapy, 126, 110082.
Hohenberg P, Kohn W. (1964). Inhomogeneous Electron Gas. Physical Review, 136, 864-871.
Jang YM, Yu CJ, Kim JS, Kim SU. (2018). Ab initio design of drug carriers for zoledronate guest molecule using phosphonated and sulfonated calix[4]arene and calix[4]resorcinarene host molecules. Journal of Materials Science, 53(7), 5125-5139.
Kadhum WR, Oshizaka T, Ichiro H, Todo H, Sugibayashi K. (2016). Usefulness of liquid-crystal oral formulations to enhance the bioavailability and skin tissue targeting of p-amino benzoic acid as a model compound. European Journal of Pharmaceutical Sciences, 88, 282-290.
Kandeel M, Abdelrahman AHM, Oh-Hashi K, Ibrahim A, Venugopala KN, Morsy MA, Ibrahim MAA. (2021). Repurposing of FDA-approved antivirals, antibiotics, anthelmintics, antioxidants, and cell protectives against SARS-CoV-2 papain-like protease. Journal of Biomolecular Structure and Dynamics, 39(14), 5129-5136.
Kohn W, Sham LJ. (1965). Self-Consistent Equations Including Exchange and Correlation Effects. Physical Review, 140(4A), 1133-1138.
Kolos M, Karlický F. (2019). Accurate many-body calculation of electronic and optical band gap of bulk hexagonal boron nitride. Physical Chemistry Chemical Physics, 21(7), 3999-4005.
Lawal A, Shaari A, Ahmed R, Jarkoni N. (2017). First-principles investigations of electron-hole inclusion effects on optoelectronic properties of Bi2Te3, a topological insulator for broadband photodetector. Physica B: Condensed Matter, 520, 69-75.
Leontie L, Danac R, Carlescu A, Doroftei C, Rusu GG, Tiron V, Gurlui S, Susu O. (2018). Electric and optical properties of some new functional lower-rim-substituted calixarene derivatives in thin films. Applied Physics A: Materials Science and Processing, 124(5), 1-12.
Lim DCK, Supian FL. (2020). Langmuir, Raman, and electrical properties comparison of calixarene and calixarene-rGO using Langmuir Blodgett (LB) technique. Journal of Materials Science: Materials in Electronics, 31, 18487-18494.
Liu D, Fan X, Dong D, Zhang Z, Yu N, Yang Z, Liu R, Liu B. (2020). Synthesis and high pressure studies of white luminescence host-guest complex nanocrystals based on C60 and p-But-calix[8]arene. Nanotechnology, 31(16), 165701.
Liu Q, Zhang TX, Zheng Y, Wang C, Kang Z, Zhao Y, Chai J, Li HB, Guo DS, Liu Y, Shi L. (2021). Calixarene-Embedded Nanoparticles for Interference-Free Gene–Drug Combination Cancer Therapy. Small, 17(8), 1-11.
Ma Y, Yoo J. (2021). History of sunscreen: An updated view. Journal of Cosmetic Dermatology, 20(4), 1044-1049.
Mingzhu L, Limei S, Shan W. (2013). First-principles study of electronic and optical properties in wurtzite ZnCoo alloys. Applied Mechanics and Materials, 333, 1847-1852.
Monkhorst H, Pack J. (1976). Special points for Brillouin zone integrations. Physical Review B, 13(12), 5188-5192.
Moussa YE, Qing Y, Ong E, Perry JD, Cheng Z, Kayser V, Cruz E, Kim RR, Sciortino N, Wheate NJ. (2018). Demonstration of In Vitro Host-Guest Complex Formation and Safety of para -Sulfonatocalix [8] arene as a Delivery Vehicle for Two Antibiotic Drugs. Journal of Pharmaceutical Sciences, 1-7.
Neopane S, Pantha N. (2019). First-Principles Study of Van Der Waals Interactions between Halogen Molecules (Cl2 and I2). Journal of Nepal Physical Society, 5(1), 19-23.
Panchal M, Kongor A, Athar M, Modi K, Patel C, Dey S, Vora M, Bhadresha K, Rawal R, Jha PC, Jain VK. (2020). Structural motifs of oxacalix[4]arene for molecular recognition of nitroaromatic explosives: Experimental and computational investigations of host-guest complexes. Journal of Molecular Liquids, 306, 112809.
Perdew JP, Burke K, Ernzerhof M. (1996). Generalized gradient approximation made simple. Physical Review Letters, 77(18), 3865-3868.
Rappe AM, Rabe KM, Kaxiras E, Joannopoulos JD. (1990). Optimized pseudopotentials. Physical Review B, 41(2), 1227-1230.
Salvador A, Chisvert A, Rodríguez A, March JG. (2003). Indirect spectrophotometric determination of p-aminobenzoic acid in sunscreen formulations by sequential injection analysis. Analytica Chimica Acta, 493(2), 233-239.
Schlegel HB. (2011). Geometry optimization. Wiley Interdisciplinary Reviews: Computational Molecular Science, 1(5), 790-809.
Sham LJ, Schlüter M. (1983). Density-Functional Theory of the Energy Gap. Physical Review Letters, 51(20), 1888-1891.
Shanuja SK, Iswarya S, Gnanamani A. (2018). Marine fungal DHICA as a UVB protectant: Assessment under in vitro and in vivo conditions. Journal of Photochemistry and Photobiology B: Biology, 179, 139-148.
Supian FL, Azahari NA, Juahir Y. (2022). Correlation of Langmuir Isotherm, Optical, Surface Potential and Morphological Characterizations of Two Functionalized Dihydroxycalix [4] arene for Lead Cation Entrapment. Journal of Microscopy, 1, 9-19.
Wang C, Chang YX, Chen X, Bai L, Wang H, Pan YC, Zhang C, Guo DS, Xue X. (2022). A Calixarene Assembly Strategy of Combined Anti-Neuroinflammation and Drug Delivery Functions for Traumatic Brain Injury Therapy. Molecules, 27(9), 2967.
Xu L, Chai J, Wang Y, Zhao X, Guo D, Shi L, Zhang Z, Liu Y. (2022). Calixarene-intergrated Nanodrug Delivery System for Tumor-targeted Delivery and Tracking of Anti-cancer Drugs In vivo. Nano Research, 15(8), 7295-7303.
Yuksel N, Köse A, Fellah MF. (2021). The supramolecularly complexes of calix[4]arene derivatives toward favipiravir antiviral drug (used to treatment of COVID-19): a DFT study on the geometry optimization, electronic structure and infrared spectroscopy of adsorption and sensing. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 101, 77-89.
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Copyright (c) 2023 Nur Farah Nadia Abd Karim, Faridah Lisa Supian, Yeong Yi Wong , Afiq Radzwan, Mazlina Musa, Amiruddin Shaari, Abdullah F. Al Naim
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