Synthesis of liquid crystalline benzothiazole based derivatives: Theoretical and experimental study of their optical and electrical properties.

Shalaw K. Salih; Rebaz M. Mustafa; Dyari M. Mamad; Kosrat N. Kaka; Rebaz A. Omer; Wali M. Hamad

doi:10.21271/ZJPAS.35.5.14

Authors

Shalaw K. Salih Department of Chemistry, Faculty of Science & Health, Koya University, Koya KOY45, Kurdistan Region – F.R. Iraq.
Rebaz M. Mustafa Department of Chemistry, Faculty of Science & Health, Koya University, Koya KOY45, Kurdistan Region – F.R. Iraq
Dyari M. Mamad University of Raparin, College of Science, Department of Physics, Sulaymaniyah, Iraq
Kosrat N. Kaka Department of Chemistry, Faculty of Science and Health, Koya University, Koya KOY45, Kurdistan Region – F.R. Iraq
Rebaz A. Omer Department of Chemistry, Faculty of Science & Health, Koya University, Koya KOY45, Kurdistan Region – F.R. Iraq.
Wali M. Hamad Department of Chemistry, Faculty of Science & Health, Koya University, Koya KOY45, Kurdistan Region – F.R. Iraq.

DOI:

https://doi.org/10.21271/ZJPAS.35.5.14

Keywords:

Synthesis, DFT, Monte Carlo, B3LYP, Bandgap Energy, Ionization Energy, Electronegativity, Electron Transfer, Adsorption, Fe (110) Crystal.

Abstract

This study describes the synthesis of 2,5-Bis(3,4-dialkoxy phenyl) Thiazolo[5,4-d} thiazoles (DAITn) (I) and its subsequent structural analysis. These compounds were prepared via reaction of dithio-oxarnidc with the freshly prepared 3,4-dialkoxy benzaldehyde in (DMF). The structure of DAITn (I) was found to have the 3 and 4 positions of the two benzene rings substituted with (OCnH2n+h n=2-5) which equaled to compound M2-M5. The primary methods used for theoretical calculations in this study are quantum mechanics/molecular dynamics simulations based on Density Functional Theory (DFT) and Monte Carlo. The Gaussian09W software's B3LYP hybrid feature and 6-311++G(d,p) basis set were employed in both the gas and aqueous phase for protonated and non-protonated species at the B3LYP level. Electronic structural identifiers were discovered from geometry-optimized structures and correlations between EHOMO (higher occupied molecular orbital energy), ELUMO (lower unoccupied molecular orbital energy), (Eg) bandgap energy, (I) ionization energy, (χ) electronegativity, (∆N) electron transfer, and (∆E_(b-d)) back-donation energy were calculated. The Monte Carlo method was used to calculate the adsorption for all identified compounds in this study, and a Fe (110) crystal more stable surface was selected. UV-visible spectroscopy is measuring absorption coefficient, transmittance, and electrical conductivity, and uses a Tauc plot for bandgap energy of the highest absorption peaks. ADTTn molecules with a wide bandgap and a high optical conductivity. Thermodynamic parameters, molecular dynamics simulations, and adsorption energy have been examining inhibitor/surface interactions with greater binding energy leading to stronger interaction and larger negative adsorption energy value indicating a more stable interaction. A four-slab model featuring eighty iron atoms per layer, or one hundred- and ten-unit cells, was used, along with a spline transformation function and a cut-off distance of 1.85 nm for nonbonded interactions. Simulated heating was employed to progressively lower the temperature and search for a low-energy adsorption site.

References

ACHAR, B. & LOKESH, K. 2004. Studies on phthalocyanine sheet polymers. Journal of organometallic chemistry, 689, 2601-2605.

AKINBULUMO, O. A., ODEJOBI, O. J. & ODEKANLE, E. L. 2020. Thermodynamics and adsorption study of the corrosion inhibition of mild steel by Euphorbia heterophylla L. extract in 1.5 M HCl. Results in Materials, 5, 100074.

AKL, A. A. 2004. Optical properties of crystalline and non-crystalline iron oxide thin films deposited by spray pyrolysis. Applied Surface Science, 233, 307-319.

AL-DOORI, H. H. & SHIHAB, M. S. 2014. Study of Some [N-substituted] p-aminoazobenzene as Corrosion Inhibitors for Mild-Steel in 1M H2SO4. Al-Nahrain Journal of Science, 17, 59-68.

AL-KUHAILI, M., SALEEM, M. & DURRANI, S. 2012. Optical properties of iron oxide (α-Fe2O3) thin films deposited by the reactive evaporation of iron. Journal of alloys and compounds, 521, 178-182.

AYDIN, H., GÜNDÜZ, B. & AYDIN, C. 2019. Surface morphology, spectroscopy, optical and conductivity properties of transparent poly (9-vinylcarbazole) thin films modified with graphene oxide. Synthetic Metals, 252, 1-7.

BOHREN, C. F. & HUFFMAN, D. R. 2008. Absorption and scattering of light by small particles, John Wiley & Sons.

BUKOWCZAN, A., HEBDA, E. & PIELICHOWSKI, K. 2021. The influence of nanoparticles on phase formation and stability of liquid crystals and liquid crystalline polymers. Journal of Molecular Liquids, 321, 114849.

CAMMI, R. & MENNUCCI, B. 1999. Linear response theory for the polarizable continuum model. The Journal of chemical physics, 110, 9877-9886.

CHATTARAJ, P. K. & ROY, D. R. 2007. Update 1 of: electrophilicity index. Chemical reviews, 107, PR46-PR74.

CHRISTOFFERSEN, E., STOLTZE, P. & NØRSKOV, J. K. 2002. Monte Carlo simulations of adsorption-induced segregation. Surface science, 505, 200-214.

DE PROFT, F. & GEERLINGS, P. 2001. Conceptual and computational DFT in the study of aromaticity. Chemical reviews, 101, 1451-1464.

EPSTEIN, R., SHEIK-BAHAE, M. & HEHLEN, M. 2009. Optical Refrigeration. Science and Applications of Laser Cooling of Solids., Wiley.

ERDOĞAN, Ş., SAFI, Z. S., KAYA, S., IŞıN, D. Ö., GUO, L. & KAYA, C. 2017. A computational study on corrosion inhibition performances of novel quinoline derivatives against the corrosion of iron. Journal of Molecular Structure, 1134, 751-761.

GALLARDO, H., MAGNAGO, R. & BORTOLUZZI, A. J. 2001. Synthesis, characterization and mesomorphic properties of Ag (I) and Pd (II) complexes containing the pyridyl and tetrazoyl rings: crystal structure of [C30H46N10Ag ClO4]. Liquid Crystals, 28, 1343-1352.

GHANBARI, A., ATTAR, M. & MAHDAVIAN, M. 2010. Corrosion inhibition performance of three imidazole derivatives on mild steel in 1 M phosphoric acid. Materials Chemistry and Physics, 124, 1205-1209.

GUO, L., ZHU, S. & ZHANG, S. 2015. Experimental and theoretical studies of benzalkonium chloride as an inhibitor for carbon steel corrosion in sulfuric acid. Journal of Industrial and Engineering Chemistry, 24, 174-180.

HA, S.-T., KOH, T.-M., LIN, H.-C., YEAP, G.-Y., WIN, Y.-F., ONG, S.-T., SIVASOTHY, Y. & ONG, L.-K. 2009. Heterocyclic benzothiazole-based liquid crystals: synthesis and mesomorphic properties. Liquid Crystals, 36, 917-925.

HAMAD, W. M., AZIZ, H. J. & AL-DUJAILI, A. H. Synthesis and liquid crystalline studies of some heterocyclic compounds with lateral long chain substituents, 2004.

HAN, J., CHANG, X. Y., ZHU, L. R., WANG, Y. M., MENG, J. B., LAI, S. W. & CHUI, S. S. Y. 2008. Synthesis and liquid crystal properties of a new class of calamitic mesogens based on substituted 2, 5‐diaryl‐1, 3, 4‐thiadiazole derivatives with wide mesomorphic temperature ranges. Liquid Crystals, 35, 1379-1394.

KOPARIR, P., OMAR, R. A., SARAC, K., AHMED, L. O., KARATEPE, A., TASKIN-TOK, T. & SAFIN, D. A. 2022. Synthesis, Characterization and Computational Analysis of Thiophene-2, 5-Diylbis ((3-Mesityl-3-Methylcyclobutyl) Methanone). Polycyclic Aromatic Compounds, 1-19.

LEBOEUF, M., KÖSTER, A. & SALAHUB, D. 1997. Approximation of the molecular electrostatic potential in a gaussian density functional method. Theoretical Chemistry Accounts, 96, 23-30.

LI, Y., CONCELLÓN, A., LIN, C.-J., ROMERO, N. A., LIN, S. & SWAGER, T. M. 2020. Thiophene-fused polyaromatics: synthesis, columnar liquid crystal, fluorescence and electrochemical properties. Chemical Science, 11, 4695-4701.

LUKOVITS, I., KALMAN, E. & ZUCCHI, F. 2001. Corrosion inhibitors—correlation between electronic structure and efficiency. Corrosion, 57, 3-8.

MAMAND, D. 2019. Theoretical calculations and spectroscopic analysis of gaussian computational examination-NMR, FTIR, UV-Visible, MEP on 2, 4, 6-Nitrophenol. Journal of Physical Chemistry and Functional Materials, 2, 77-86.

MAMAND, D. M. & QADR, H. M. 2021. Comprehensive spectroscopic and optoelectronic properties of bbl organic semiconductor. Protection of Metals and Physical Chemistry of Surfaces, 57, 943-953.

MAMAND, D. M. & QADR, H. M. 2022. Density Functional Theory and Computational Simulation of the Molecular Structure on Corrosion of Carbon Steel in Acidic Media of Some Amino Acids. Russian Journal of Physical Chemistry A, 96, 2155-2165.

MAMAND, D. M., RASUL, H. H., OMER, P. K. & QADR, H. M. 2022. Theoretical and experimental investigation on ADT organic semiconductor in different solvents. Condensed Matter and Interphases, 24, 227-242.

MATHARU, A. & CHAMBERS‐ASMAN, D. 2007. Structure–property investigation of 2‐and 3‐thienylacrylates bearing laterally fluorinated azobenzene moieties. Liquid Crystals, 34, 1317-1336.

MAURYA, A. & AWASTHI, D. K. 2022. An Introduction to Liquid Crystals and It’s Types Nematic, Smetic and Cholestric Crystals. International Research Journal of Innovations in Engineering and Technology, 6, 101.

NAFEE, S. S., AHMED, H. & HAGAR, M. 2020. Theoretical, experimental and optical study of new thiophene-based liquid crystals and their positional isomers. Liquid Crystals, 47, 1291-1302.

OBOT, I. & OBI-EGBEDI, N. 2010. Adsorption properties and inhibition of mild steel corrosion in sulphuric acid solution by ketoconazole: experimental and theoretical investigation. Corrosion Science, 52, 198-204.

OMER, R., KOPARIR, P., KOPARIR, M., RASHID, R., AHMED, L. & HAMA, J. 2022a. Synthesis, Characterization and DFT Study of 1-(3-Mesityl-3-methylcyclobutyl)-2-((4-phenyl-5-(thiophen-2-yl)-4H-1, 2, 4-triazol-3-yl) thio) ethan-1-one. Protection of Metals and Physical Chemistry of Surfaces, 1-13.

OMER, R. A., KOPARIR, P. & AHMED, L. 2022b. Theoretical determination of corrosion inhibitor activities of 4-allyl-5-(pyridin-4-yl)-4H-1, 2, 4-triazole-3-thiol-thione tautomerism. Indian Journal of Chemical Technology (IJCT), 29, 75-81.

OMER, R. A., KOPARIR, P. & AHMED, L. O. 2022c. Characterization and inhibitor activity of two newly synthesized thiazole. Journal of Bio-and Tribo-Corrosion, 8, 28.

ONG, L.-K., HA, S.-T., YEAP, G.-Y. & LIN, H.-C. 2018. Heterocyclic pyridine-based liquid crystals: synthesis and mesomorphic properties. Liquid Crystals, 45, 1574-1584.

OREK, C., GÜNDÜZ, B., KAYGILI, O. & BULUT, N. 2017. Electronic, optical, and spectroscopic analysis of TBADN organic semiconductor: Experiment and theory. Chemical Physics Letters, 678, 130-138.

OU, Z., SHEN, J. & KADISH, K. M. 2006. Electrochemistry of Aluminum Phthalocyanine: Solvent and Anion Effects on UV− Visible Spectra and Reduction Mechanisms. Inorganic chemistry, 45, 9569-9579.

PARLAK, A. E., OMAR, R. A., KOPARIR, P. & SALIH, M. I. 2022. Experimental, DFT and Theoretical Corrosion Study for 4-(((4-ethyl-5-(thiophen-2-yl)-4H-1, 2, 4-triazole-3-yl) thio) methyl)-7, 8-dimethyl-2H-chromen-2-one. Arabian Journal of Chemistry, 15, 104088.

PARRA, M., ELGUETA, E., ULLOA, J., VERGARA, J. & SANCHEZ, A. 2012. Columnar liquid crystals based on amino-1, 3, 4-thiadiazole derivatives. Liquid Crystals, 39, 917-925.

PETROV, V., PAVLUCHENKO, A. & SMIRNOVA, N. 1995. New liquid crystalline pyridine derivatives. Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals, 265, 47-53.

PLATSCHEK, B. 2007. Ordered Mesoporous Silica: Control of Morphology and Exploration with Single Molecules. lmu.

QADR, H. M. & MAMAND, D. Monte Carlo calculation of absorbed dose under MeV proton irradiation. Journal of Physical Chemistry and Functional Materials, 5, 7-11.

QADR, H. M. & MAMAND, D. M. 2021. Molecular structure and density functional theory investigation corrosion inhibitors of some oxadiazoles. Journal of Bio-and Tribo-Corrosion, 7, 140.

QIANG, Y., ZHANG, S., GUO, L., ZHENG, X., XIANG, B. & CHEN, S. 2017. Experimental and theoretical studies of four allyl imidazolium-based ionic liquids as green inhibitors for copper corrosion in sulfuric acid. Corrosion Science, 119, 68-78.

RAICHEVA, S., ALEKSIEV, B. & SOKOLOVA, E. 1993. The effect of the chemical structure of some nitrogen-and sulphur-containing organic compounds on their corrosion inhibiting action. Corrosion Science, 34, 343-350.

RAMALINGAM, S., BABU, P. D. S., PERIANDY, S. & FEREYDUNI, E. 2011. Vibrational investigation, molecular orbital studies and molecular electrostatic potential map analysis on 3-chlorobenzoic acid using hybrid computational calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 84, 210-220.

RAVINDRA, N., GANAPATHY, P. & CHOI, J. 2007. Energy gap–refractive index relations in semiconductors–An overview. Infrared physics & technology, 50, 21-29.

RAYSSI, C., KOSSI, S. E., DHAHRI, J. & KHIROUNI, K. 2018. Frequency and temperature-dependence of dielectric permittivity and electric modulus studies of the solid solution Ca 0.85 Er 0.1 Ti 1− x Co 4x/3 O 3 (0≤ x≤ 0.1). Rsc Advances, 8, 17139-17150.

REBAZ, O., KOPARIR, P., QADER, I. & AHMED, L. 2022. Theoretical Determination of Corrosion Inhibitor Activities of Naphthalene and Tetralin. Gazi University Journal of Science, 1-1.

SASSI, M., OUESLATI, A., MOUTIA, N., KHIROUNI, K. & GARGOURI, M. 2017. A study of optical absorption and dielectric properties in lithium chromium diphosphate compound. Ionics, 23, 847-855.

SEED, A. 2007. Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core. Chemical Society Reviews, 36, 2046-2069.

SHAHBAZI, H., TATAEI, M., ENAYATI, M., SHAFEIEY, A. & MALEKABADI, M. A. 2019. Structure-transmittance relationship in transparent ceramics. Journal of Alloys and Compounds, 785, 260-285.

SHAN, H., ZHANG, H., LIU, J., WANG, S., MA, X., ZHANG, L., LIU, D., XIE, C. & TAO, Z. Retrieval method of aerosol extinction coefficient profile by an integral lidar system and case study. Fourth Seminar on Novel Optoelectronic Detection Technology and Application, 2018. International Society for Optics and Photonics, 106971D.

SHARMA, V. S., SHAH, A. P. & SHARMA, A. S. 2019. A new class of supramolecular liquid crystals derived from azo calix [4] arene functionalized 1, 3, 4-thiadiazole derivatives. New Journal of Chemistry, 43, 3556-3564.

SINGH, S. 2000. Phase transitions in liquid crystals. Physics Reports, 324, 107-269.

TEOH, W.-J., TUN NUR ISKANDAR, N. A. J., YEAP, G.-Y., KANEKO, K., SHIMIZU, A. & ITO, M. M. 2022. Experimental and computational studies of laterally ethoxy Schiff base-ester liquid crystalline magnets. Liquid Crystals, 49, 875-885.

TODORAN, D., TODORAN, R., SZAKÁCS, Z. & ANITAS, E. 2018. Electrical conductivity and optical properties of pulsed laser deposited LaNi5 nanoscale films. Materials, 11, 1475.

TOFT, J. & KVALHEIM, O. M. 1993. Eigenstructure tracking analysis for revealing noise pattern and local rank in instrumental profiles: application to transmittance and absorbance IR spectroscopy. Chemometrics and intelligent laboratory systems, 19, 65-73.

TOMI, I. H. R., AL-KARAWI, A. J. M., OMARALI, A.-A. B. & AL-HEETIMI, D. T. 2021. Liquid crystal behavior of Ag (I) complexes based on a series of mesogenic 1, 3, 4-thiadiazole ligands. Molecular Crystals and Liquid Crystals, 722, 8-26.

TRIPATHY, S. 2015. Refractive indices of semiconductors from energy gaps. Optical materials, 46, 240-246.

TURAN, N., KAYA, E., GÜNDÜZ, B., ÇOLAK, N. & KÖRKOCA, H. 2012. Synthesis, characterization of poly (E)-3-amino-4-((3-bromophenyl) diazenyl)-1H-pyrazol-5-ol: Investigation of antibacterial activity, fluorescence, and optical properties. Fibers and Polymers, 13, 415-424.

VARDAR, D., AKDAŞ KıLıÇ, H., OCAK, H., JEANNIN, O., CAMEREL, F. & ERAN, B. B. 2021. Pyridine-based chiral smectogens: effects of polar end groups on liquid crystal properties. Liquid Crystals, 48, 616-625.

WU, L.-H., WANG, Y.-C. & HSU, C.-S. 2000. Synthesis and characterization of thiophene-containing liquid crystals. Liquid Crystals, 27, 1503-1513.

XIE, P., WANG, Z., ZHANG, Z., FAN, R., CHENG, C., LIU, H., LIU, Y., LI, T., YAN, C. & WANG, N. 2018. Silica microsphere templated self-assembly of a three-dimensional carbon network with stable radio-frequency negative permittivity and low dielectric loss. Journal of Materials Chemistry C, 6, 5239-5249.

YANG, K., HUANG, X., HUANG, Y., XIE, L. & JIANG, P. 2013. Fluoro-polymer@ BaTiO3 hybrid nanoparticles prepared via RAFT polymerization: toward ferroelectric polymer nanocomposites with high dielectric constant and low dielectric loss for energy storage application. Chemistry of Materials, 25, 2327-2338.

YEAP, G. Y., HA, S. T., LIM, P. L., BOEY, P. L., ITO, M. M., SANEHISA, S. & YOUHEI, Y. 2006. Synthesis, physical and mesomorphic properties of Schiff's base esters containing ortho‐, meta‐and para‐substituents in benzylidene‐4′‐alkanoyloxyanilines. Liquid crystals, 33, 205-211.

YEAP*, G.-Y., HA, S.-T., LIM, P.-L., BOEY, P.-L., MAHMOOD, W. A. K., ITO, M. M. & SANEHISA, S. 2004. Synthesis and mesomorphic properties of Schiff base esters ortho-hydroxy-para-alkyloxybenzylidene-para-substituted anilines. Molecular Crystals and Liquid Crystals, 423, 73-84.

YOSHINO, K., OYAMA, S. & YONETA, M. 2008. Structural, optical and electrical characterization of undoped ZnMgO film grown by spray pyrolysis method. Journal of Materials Science: Materials in Electronics, 19, 203-209.