TY  - JOUR
T1  - Structural, Vibrational, and Electronic Properties of 2,5-Bis(1-Naphthyl)-1,3,4-Oxadiazole: Experimental and Theoretical Investigation
TT  - 2,5-Bis(1-Naftil)-1,3,4-Oksadiazole'nin Yapı, Titreşim ve Elektronik Özellikleri: Deneysel ve Teorik Araştırma
AU  - Babur Şaş, Emine
AU  - Kurt, Mustafa
PY  - 2025
DA  - October
Y2  - 2025
DO  - 10.35414/akufemubid.1643029
JF  - Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi
PB  - Afyon Kocatepe Üniversitesi
WT  - DergiPark
SN  - 2149-3367
SP  - 1032
EP  - 1039
VL  - 25
IS  - 5
LA  - en
AB  - This study used both theoretical and experimental methods to examine the structural, vibrational, and electrical characteristics of the 2,5-Bis(1-naphthyl)-1,3,4-oxadiazole (BND) molecule. The vibrational wave numbers, bond lengths, and bond angles of the optimized molecular structure were examined and compared to the experimental results. Plots of the correlation between the recorded FT-IR and FT-Raman spectra and the Density Functional Theory (DFT) computations were created. Furthermore, chemical shift values were theoretically predicted using the GIAO method in THF solvent and NMR spectra were collected; these values demonstrated a satisfactory correlation with the experimental values. The frontier molecular orbitals (HOMO-LUMO) were analyzed to assess the electronic properties, and a sizable energy gap that demonstrated the molecule's stability was discovered. The charge distribution and active spots in the molecule were revealed by 2D contours and molecular electrostatic potential (MEP) surface analysis.
KW  - FT-IR
KW  - FT-Raman
KW  - NMR
KW  - HOMO-LUMO
KW  - MEP
N2  - Bu çalışmada, 2,5-Bis(1-naftil)-1,3,4-oksadiazol (BND) molekülünün yapısal, titreşim ve elektriksel özellikleri hem teorik hem de deneysel yöntemlerle incelenmiştir. Optimize edilmiş moleküler yapının titreşim dalga sayıları, bağ uzunlukları ve bağ açıları incelenmiş ve deneysel sonuçlarla karşılaştırılmıştır. Kaydedilen FT-IR ve FT-Raman spektrumları ile Yoğunluk Fonksiyonel Teorisi (DFT) hesaplamaları arasındaki korelasyon grafikleri oluşturulmuştur. Ayrıca, kimyasal kayma değerleri THF çözücüsünde GIAO yöntemi kullanılarak teorik olarak tahmin edilmiş ve NMR spektrumları toplanmıştır; bu değerler deneysel değerlerle tatmin edici bir korelasyon göstermiştir. Elektronik özellikleri değerlendirmek için sınır moleküler orbitalleri (HOMO-LUMO) analiz edilmiş ve molekülün kararlılığını gösteren önemli bir enerji boşluğu keşfedilmiştir. Moleküldeki yük dağılımı ve aktif noktalar 2B konturlar ve moleküler elektrostatik potansiyel (MEP) yüzey analizi ile ortaya çıkarılmıştır.
CR  - Andzelm, J., & Wimmer, E. 1992. Density functional Gaussian‐type‐orbital approach to molecular geometries, vibrations, and reaction energies. The Journal of chemical physics, 96(2), 1280-1303.
https://doi.org/10.1063/1.462165
CR  - Bajaj, S., Asati, V., Singh, J., & Roy, P. P., 2015. 1, 3, 4-Oxadiazoles: An emerging scaffold to target growth factors, enzymes and kinases as anticancer agents. European journal of medicinal chemistry, 97, 124-141.
https://doi.org/10.1016/j.ejmech.2015.04.051
CR  - Becke, A. D. 1992. Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction. The Journal of chemical physics, 96(3), 2155-2160.
https://doi.org/10.1063/1.462066
CR  - Bouklah, M., Hammouti, B., Benkaddour, M., & Benhadda, T., 2005. Thiophene derivatives as effective inhibitors for the corrosion of steel in 0.5 m H2 SO4. Journal of Applied Electrochemistry, 35, 1095-1101.
https://doi.org/10.1007/s10800-005-9004-z
CR  - Chang, C. H., Griniene, R., Su, Y. D., Yeh, C. C., Kao, H. C., Grazulevicius, J. V., ... & Grigalevicius, S. 2015. Efficient red phosphorescent OLEDs employing carbazole-based materials as the emitting host. Dyes and Pigments, 122, 257-263.
https://doi.org/10.1016/j.dyepig.2015.06.038
CR  - Chebabe, D., Chikh, Z. A., Hajjaji, N., Srhiri, A., & Zucchi, F., 2003. Corrosion inhibition of Armco iron in 1 M HCl solution by alkyltriazoles. Corrosion science, 45(2), 309-320.
https://doi.org/10.1016/S0010-938X(02)00098-7
CR  - Ditchfield, R. 1972. Molecular orbital theory of magnetic shielding and magnetic susceptibility. The Journal of Chemical Physics, 56(11), 5688-5691.
https://doi.org/10.1063/1.1677088
CR  - El-Azhary, A. A. 1996. Vibrational analysis of the spectra of 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole, 1, 2, 5-oxadiazole and 1, 2, 5-thiadiazole: comparison between DFT, MP2 and HF force fields. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 52(1), 33-44.
https://doi.org/10.1016/0584-8539(95)01535-3
CR  - El-Rehim, S. A., Ibrahim, M. A., & Khaled, K. F., 1999. 4-Aminoantipyrine as an inhibitor of mild steel corrosion in HCl solution. Journal of Applied Electrochemistry, 29, 593-599.
https://doi.org/10.1023/A:1003450818083
CR  - Fang, J., & Li, J. 2002. Quantum chemistry study on the relationship between molecular structure and corrosion inhibition efficiency of amides. Journal of Molecular Structure: THEOCHEM, 593(1-3), 179-185.
https://doi.org/10.1016/S0166-1280(02)00316-0
CR  - Fleming I., 1976. Frontier Orbitals and Organic Chemical Reactions, Wiley, London.
CR  - Fouda, A. S., Al-Sarawy, A. A., & El-Katori, E. E., 2006. Pyrazolone derivatives as corrosion inhibitors for C-steel in hydrochloric acid solution. Desalination, 201(1-3), 1-13.
https://doi.org/10.1016/j.desal.2006.03.519
CR  - Foroumadi, A., Mansouri, S., Kiani, Z., & Rahmani, A., 2003. Synthesis and in vitro antibacterial evaluation of N-[5-(5-nitro-2-thienyl)-1, 3, 4-thiadiazole-2-yl] piperazinyl quinolones. European journal of medicinal chemistry, 38(9), 851-854.
https://doi.org/10.1016/S0223-5234(03)00148-X
CR  - Frisch, M. J. E. A., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., ... & Fox, D. J. 2009. gaussian 09, Gaussian. Inc., Wallingford CT, 121, 150-166.
CR  - Hohenberg, P., & Kohn, W. 1964. Inhomogeneous electron gas. Physical review, 136(3B), B864.
https://doi.org/10.1103/PhysRev.136.B864
CR  - Fuentealba, P., Pérez, P., & Contreras, R. 2000. On the condensed Fukui function. The Journal of Chemical Physics, 113(7), 2544-2551.
https://doi.org/10.1063/1.1305879
CR  - Holla, B. S., Veerendra, B., Shivananda, M. K., & Poojary, B., 2003. Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1, 2, 4-triazoles. European Journal of Medicinal Chemistry, 38(7-8), 759-767.
https://doi.org/10.1016/S0223-5234(03)00128-4
CR  - Hosseini, S. M. A., & Azimi, A., 2009. The inhibition of mild steel corrosion in acidic medium by 1-methyl-3-pyridin-2-yl-thiourea. Corrosion Science, 51(4), 728-732.
https://doi.org/10.1016/j.corsci.2008.11.019
CR  - Huangzhong, Y. 2010. Different solvents effect on the performance of the solar cells based on poly (3-hexylthiophene):methanofullerenes. Synthetic Metals, 160(23-24), 2505-2509.
https://doi.org/10.1016/j.synthmet.2010.09.035
CR  - Hughes, G., & Bryce, M. R. 2005. Electron-transporting materials for organic electroluminescent and electrophosphorescent devices. Journal of Materials Chemistry, 15(1), 94-107
https://doi.org/10.1039/B413249C
CR  - Jeon, B. C., Kim, M. S., Cho, M. J., Choi, D. H., Ahn, K. S., & Kim, J. H. 2014. Effect of solvent on dye-adsorption process and photovoltaic properties of dendritic organic dye on TiO2 electrode of dye-sensitized solar cells. Synthetic metals, 88, 130-135.
https://doi.org/10.1016/j.synthmet.2013.12.006
CR  - Kalinowski, H. O., Berger, S., & Braun, S. 1988. Carbon-13 NMR spectroscopy. John Wiley and Sons, New York.
CR  - Krishnakumar, V., & Xavier, R. J. 2003. Normal coordinate analysis of vibrational spectra of 2-methylindoline and 5-hydroxyindane. Indian Journal of Pure & Applied Physics, 41, 95-99.
CR  - Krukiewicz, K., Jarosz, T., Herman, A. P., Turczyn, R., Boncel, S., & Zak, J. K. 2016. The effect of solvent on the synthesis and physicochemical properties of poly (3, 4-ethylenedioxypyrrole). Synthetic Metals, 217, 231-236.
https://doi.org/10.1016/j.synthmet.2016.04.005
CR  - Lagrenee, M., Mernari, B., Chaibi, N., Traisnel, M., Vezin, H., & Bentiss, F., 2001. Investigation of the inhibitive effect of substituted oxadiazoles on the corrosion of mild steel in HCl medium. Corrosion science, 43(5), 951-962.
https://doi.org/10.1016/S0010-938X(00)00076-7
CR  - Munoz-Caro, C., Nino, A., Senent, M. L., Leal, J. M., & Ibeas, S. 2000. Modeling of protonation processes in acetohydroxamic acid. The Journal of organic chemistry, 65(2), 405-410.
https://doi.org/10.1021/jo991251x
CR  - Peng, Z., Bao, Z., & Galvin, M. E. 1998. Oxadiazole‐Containing Conjugated Polymers for Light‐Emitting Diodes. Advanced Materials, 10(9), 680-684.
https://doi.org/10.1002/(SICI)1521-4095(199806)10:9 <680::AID-ADMA680>3.0.CO;2-H
CR  - Politzer, P., Laurence, P. R., & Jayasuriya, K. 1985. Molecular electrostatic potentials: an effective tool for the elucidation of biochemical phenomena. Environmental health perspectives, 61, 191-202.
https://doi.org/10.1289/ehp.8561191
CR  - Reddy, M. A., Mallesham, G., Thomas, A., Srinivas, K., Rao, V. J., Bhanuprakash, K., ... & Srivastava, R. 2011. Synthesis and characterization of novel 2, 5-diphenyl-1, 3, 4-oxadiazole derivatives of anthracene and its application as electron transporting blue emitters in OLEDs. Synthetic metals, 161(9-10), 869-880.
https://doi.org/10.1016/j.synthmet.2011.02.015
CR  - Reig, M., Gozálvez, C., Bujaldón, R., Bagdziunas, G., Ivaniuk, K., Kostiv, N., ... & Velasco, D. 2017. Easy accessible blue luminescent carbazole-based materials for organic light-emitting diodes. Dyes and Pigments, 137, 24-35.
https://doi.org/10.1016/j.dyepig.2016.09.062
CR  - Rodríguez-Valdez, L. M., Martínez-Villafañe, A., & Glossman-Mitnik, D. 2005. CHIH-DFT theoretical study of isomeric thiatriazoles and their potential activity as corrosion inhibitors. Journal of Molecular Structure: THEOCHEM, 716(1-3), 61-65.
https://doi.org/10.1016/j.theochem.2004.10.082
CR  - Romano, E., Soria, N. A. J., Rudyk, R., & Brandán, S. A. 2012. Theoretical study of the infrared spectrum of 5-phenyl-1, 3, 4-oxadiazole-2-thiol by using DFT calculations. Molecular Simulation, 38(7), 561-566.
https://doi.org/10.1080/08927022.2011.640936
CR  - Sas, E. B., Kurban, M., Gündüz, B., & Kurt, M. 2018. Photophysical, spectroscopic properties and electronic structure of BND: Experiment and theory. Synthetic Metals, 246, 39-44.
https://doi.org/10.1016/j.synthmet.2018.09.013
CR  - Scrocco, E., & Tomasi, J. 1978. Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials. In Advances in quantum chemistry,Vol. 11, pp. 115-193, Academic Press.
https://doi.org/10.1016/S0065-3276(08)60236-1
CR  - Singh, N. P., & Yadav, R. A. 2001. Vibrational studies of trifluoromethyl benzene derivatives 1: 2-amino, 5-chloro and 2-amino, 5-bromo benzotrifluorides. Indian Journal of Physics, 75, 347-355.
CR  - Singh, N. K., Butcher, R. J., Tripathi, P., Srivastava, A. K., & Bharty, M. K. 2007. 5-Phenyl-1, 3, 4-oxadiazole-2 (3H)-thione. Acta Crystallographica Section E: Structure Reports Online, 63(2), o782-o784.
https://doi.org/10.1107/S1600536806052238
CR  - Stephens, P. J., Devlin, F. J., Chabalowski, C. F., & Frisch, M. J. 1994. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. The Journal of physical chemistry, 98(45), 11623-11627.
https://doi.org/10.1021/j100096a001
CR  - Şaş, E. B., Çifçi, S., & Kurt, M. 2022. Spectroscopic Characterization and DFT Calculations on 1H-benzimidazole-2-carboxylic acid monohydrate Molecule. Sakarya University Journal of Science, 26(5), 879-891.
https://doi.org/10.16984/saufenbilder.1100391
CR  - Tanış, E., Babur Sas, E., Gündüz, B., & Kurt, M. 2018. Required theoretical and experimental physical characteristics of tris [4-(diethylamino) phenyl] amine organic material. Journal of Materials Science: Materials in Electronics, 29, 16111-16119.
https://doi.org/10.1007/s10854-018-9700-1
Tao, Y., Yang, C., & Qin, J. 2011. Organic host materials for phosphorescent organic light-emitting diodes. Chemical Society Reviews, 40(5), 2943-2970.
https://doi.org/10.1039/C0CS00160K
CR  - Tokuhisa, H., Era, M., Tsutsui, T., & Saito, S. 1995. Electron drift mobility of oxadiazole derivatives doped in polycarbonate. Applied physics letters, 66(25), 3433-3435.
https://doi.org/10.1063/1.113378
CR  - Varsányi, G. 2012. Vibrational spectra of benzene derivatives. Elsevier.
CR  - Wolinski, K., Hinton, J. F., & Pulay, P. 1990. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112(23), 8251-8260.
https://doi.org/10.1021/ja00179a005
CR  - Yang, X., Xu, X., & Zhou, G. 2015. Recent advances of the emitters for high performance deep-blue organic light-emitting diodes. Journal of Materials Chemistry C, 3(5), 913-944.
https://doi.org/10.1039/C4TC02474E
CR  - https://cccbdb.nist.gov/vibscalejustx.asp (13.02.2025)
UR  - https://doi.org/10.35414/akufemubid.1643029
L1  - https://dergipark.org.tr/tr/download/article-file/4623784
ER  -