Bis-Kalkon Türevlerinin Elektrokimyasal Davranışlarının İncelenmesi

Yıl 2020, , 53 - 61, 03.06.2020

Neslihan Nohut Maşlakcı , Ali Kömür , Abdullah Biçer , Günseli Turgut Cin , Ayşegül Öksüz

https://doi.org/10.29048/makufebed.668313

Cited By: 1

Öz

Bis-kalkon
türevleri olarak bilinen (2E,5E)-2,5-dibenzilidensiklopentanon (P1) ve (2E,5E)-2,5-bis (4-nitrobenziliden)
siklopentanonun (P2) elektrokimyasal
davranışı çalışma elektrotu olarak bir indiyum kalay oksit (ITO) kullanılarak
döngüsel voltametri ile incelenmiştir. Tekrarlanan döngüsel voltammogram
ölçümleri bis-kalkon türevleri için mükemmel uzun süreli redoks stabilitesi
sergilemiştir. P1'in 1. döngüsü için
anodik bölgedeki oksidasyon piki -0.20 V'de görülürken, P2'nin oksidasyon piki -0.47 V'de gözlenmiştir. Öte yandan, P2 yapısında benzen halkası üzerinde p-konumunda elektron çekici NO₂
grubunun varlığı, en yüksek dolu moleküler orbital (HOMO) ve en düşük boş
moleküler orbital (LUMO) enerji aralığında bir artışa neden olmuştur. ITO cam
substratlar üzerine kaplanan P1 ve P2 filmlerinin yüzey morfolojisi ve
yapısal özellikleri, taramalı elektron mikroskopisi (SEM) ve enerji dağıtıcı X-ışını
spektroskopisi (EDS) kullanılarak incelenmiştir. SEM mikrografları, P1 ve P2'nin ITO yüzeyi üzerinde homojen bir şekilde dağıldığını
göstermiştir. CV ölçümünden sonra, P2'nin
tane boyutunun artan ITO yüzey pürüzlülüğü ile arttığı gözlenmiştir. Ayrıca EDS
sonuçları, ITO yüzeyi üzerinde P1 ve
P2'nin varlığını doğrulamıştır.

Anahtar Kelimeler

Bis-kalkon türevleri, döngüsel voltametri, elektrokimya

To Investigate the Electrochemical Behaviors of Bis-Chalcone Derivatives

Öz

The electrochemical behavior
of (2E,5E)-2,5-dibenzylidenecyclopentanone (P1) and (2E,5E)-2,5-bis(4-nitrobenzylidene)cyclopentanone (P2) known as bis-chalcone derivatives
was studied by cyclic voltammetry (CV) using an indium tin oxide (ITO) as the
working electrode. Repeated cyclic voltammograms measurements exhibited
excellent long-term redox stability for bis-chalcone derivatives. The oxidation
peak for in the anodic region for the 1st cycle of the P1 appeared at -0.20 V, while the oxidation peak of P2 was observed at -0.47 V. On the
other hand, the existence of the electron attracting NO₂ group at p-position on the benzene ring in the structure
of P2 caused an increase in the
highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular
orbital (LUMO) energy gap. The surface morphology and structural features of P1 and P2 films coated onto ITO glass substrates were investigated by
using scanning electron microscopy (SEM) and energy-dispersive X-ray
spectroscopy (EDS). SEM micrographs demonstrated that the P1 and P2 were
homogeneously distributed over the ITO surface. After CV measurement, it was
observed that the grain size of P2 increased
with increasing ITO surface roughness. Moreover, the EDS results confirmed the
presence of P1 and P2 on the ITO surface.

Anahtar Kelimeler

Bis-chalcone derivatives, cyclic voltammetry, electrochemistry

Kaynakça

• Al-Ayed, A. S. (2011). Synthesis, spectroscopy and electrochemistry of new 3-(5-aryl-4,5-dihydro-1H- pyrazol-3-yl)-4-hydroxy-2H-chromene-2-one 4,5 as a novel class of potential anti-bacterial and antioxidant derivatives. International Journal of Organic Chemistry, 1, 87-96.
• Albuquerque, H. M. T., Santos, C. M. M., Cavaleiro, J. A. S., Silva, A. M. S. (2014). Chalcones as versatile synthons for the synthesis of 5- and 6-membered nitrogen heterocycles. Current Organic Chemistry, 18, 2750-2775.
• Asiri, A. M., Marwani, H. M., Alamry, K. A., Al-Amoudi, M. S., Khan, S. A., El-Daly, S. A. (2014). Green synthesis, characterization, photophysical and electrochemical properties of bis-chalcones. International Journal of Electrochemical Science, 9, 799-809.
• Biradar, J. S., Sasidhar, B. S., Parveen, R. (2010). Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. European Journal of Medicinal Chemistry, 45, 4074-4078.
• Bukhari, S. N. A., Jasamai, M., Jantan, I., Ahmad, W. (2013). Review of methods and various catalysts used for chalcone synthesis. Mini-Reviews in Organic Chemistry, 10, 73-83.
• Cogal, S., Ocakoglu, K., Uygun Oksuz, A. (2014). The synthesis, photophysical and electrochemical studies of symmetrical phthalocyanines linked thiophene substituents. Inorganica Chimica Acta, 423, 139-144.
• Ducki, S., Forrest, R., Hadfield, J. A., Kendall, A., Lawrence, N. J., McGown, A. T., Rennison, D. (1998). Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorganic & Medicinal Chemistry Letters, 8, 1051-1056.
• Erasmus, E. (2011). Ferrocene- and ruthenocene-containing chalcones: A spectroscopic and electrochemical study. Inorganica Chimica Acta, 378, 95-101.
• Fayed, T. A. (2006). A novel chalcone-analogue as an optical sensor based on ground and excited states intramolecular charge transfer: A combined experimental and theoretical study. Chemical Physics, 324(2-3), 631-638.
• Jin, H., Li, X., Tan, T., Wang, S., Xiao, Y., Tian, J. (2014). Electrochromic properties of novel chalcones containing triphenylamine moiety. Dyes and Pigments, 106, 154-160.
• Ju, K. -S., Parales, R. E. (2010). Nitroaromatic compounds, from synthesis to biodegradation. Microbiology and Molecular Biology Reviews, 74(2), 250-272.
• Katsori, A. M., Hadjipavlou-Litina, D. (2009). Chalcones in cancer: Understanding their role in terms of QSAR. Current Medicinal Chemistry, 16(9), 1062-1081.
• Konieczny, M. T., Konieczny, W., Sabisz, M., Skladanowski, A., Wakieć, R., Augustynowicz-Kopeć, E., Zwolska, Z. (2007). Acid-catalyzed synthesis of oxathiolone fused chalcones.
• Comparison of their activity toward various microorganisms and human cancer cells line. European Journal of Medicinal Chemistry, 42, 729-733.
• Kumar, D., Kumar, N. M., Akamatsu, K., Kusaka, E., Harada, H., Ito, T. (2010). Synthesis and biological evaluation of indolyl chalcones as antitumor agents. Bioorganic & Medicinal Chemistry Letters, 20, 3916-3919.
• Kumar, A., Singh, D., Kaur, D. (2009). Grain size effect on structural, electrical and mechanical properties of NiTi thin films deposited by magnetron co-sputtering. Surface & Coatings Technology, 203, 1596-1603.
• Kwong, H. C., Sim, A., Chidan Kumar, C. S., Then, L. Y., Win, Y. –F., Quah, C. K., Naveen, S., Warad, I. (2017). Crystal structure and Hirshfeld surface analysis of (2E,2′E )-3,3′-(1,4-phenylene)bis[1-(2,4-difluorophenyl)prop-2-en-1-one]. Acta Crystallographica Section E Crystallographic Communications, 73(12), 1812-1816.
• Li, J. –T., Yang, W. –Y., Chen, G. –F., Li, T. –S. (2003). A facile synthesis of α,α’-bis(substituted benzylidene) cycloalkanones catalyzed by KF/Al2O3 under ultrasound irradiation. Synthetic Communications, 33(15), 2619-2625.
• Mahdavinia, G. H., Mirzazadeh, M. (2012). Fast, facile and convenient synthesis of α,α-bis(substituted-arylidene)cycloalkanones: An improved protocol. E-Journal of Chemistry, 9(1), 49-54.
• Motiur Rahman, A. F. M., Jeong, B. –S., Kim, D. H., Park, J. K., Lee, E. S., Jahng, Y. (2007). A facile synthesis of a,a'-bis(substituted-benzylidene)-cycloalkanones and substituted-benzylidene heteroaromatics: Utility of NaOAc as a catalyst for aldol-type reaction. Tetrahedron, 63, 2426-2431.
• Muto, T., Temma, T., Kimura, M., Hanabusa, K., Shirai, H. (2001). Elongation of the π-system of phthalocyanines by introduction of thienly substituents at the peripheral β positions. Synthesis and characterization. Journal of Organic Chemistry, 66(18), 6109-6115.
• Naik, K. M., Nandibewoor, T.S. (2012). Electrochemical behavior of chalcone at a glassy carbon electrode and its analytical applications. American Journal of Analytical Chemistry, 3, 656-663.
• Nohut Maşlakcı, N., Biçer, A., Turgut Cin, G., Uygun Öksüz, A. (2018). Electrochromic properties of some bis-chalcone derivatives-based nanofibers. Journal of Applied Polymer Science, 135(46010), 1-11.
• Nowakowska, Z. (2007). A review of anti-infective and anti-inflammatory chalcones. European Journal of Medicinal Chemistry, 42, 125-137.
• Pammi, S. V. N., Jung, H. –J., Yoon, S. –G. (2011). Low-temperature nanocluster deposition (NCD) for improvement of the structural, electrical, and optical properties of ITO thin films. IEEE Transactions on Nanotechnology, 10(5), 1059-1065.
• Quintana-Espinoza, P., Yanez, C., Escobar, C. A., Sicker, D., Araya-Maturana, R., Squella, J. A. (2006). Electrochemical approach to the radical anion formation from 2’-hydroxy chalcone derivatives. Electroanalysis, 18, 521-525.
• Rane, R. A., Telekar, V. N. (2010). Synthesis and evaluation of novel chloropyrrole molecules designed by molecular hybridization of common pharmacophores as potential antimicrobial agents. Bioorganic & Medicinal Chemistry Letters, 20, 5681-5685.
• Ritter, M., Martins, R. M., Dias, D., Pereira, C. M. P. (2014). Recent advances on the synthesis of chalcones with antimicrobial activities: A brief review. Letters in Organic Chemistry, 11, 498-508.
• Saby, C., Ortiz, B., Champagne, G. Y., Bélanger, D. (1997). Electrochemical modification of glassy carbon electrode using aromatic diazonium salts. 1. Blocking effect of 4-nitrophenyl and 4-carboxyphenyl groups. Langmuir, 13, 6805-6813.
• Selinova, D. G., Gorbunov, A. A., Mayorova, O. A., Vasyanin, A. N., Lunegov, I. V., Shklyaeva, E. V., Abashev, G. G. (2017). New electroactive asymmetrical chalcones and there from derived 2-amino-/2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties. Beilstein Journal of Organic Chemistry, 13, 1583-1595.
• Si, Z. K., Zhang, Q., Xue, M. Z., Sheng, Q. R., Liu, Y. G. (2011). Novel UV-sensitive bis-chalcone derivatives: Synthesis and photocrosslinking properties in solution and solid PMMA film. Research on Chemical Intermediates, 37(6), 635-646.
• Tala-Tapeh, S. M., Mahmoodi, N., Vaziri, A. (2015). Synthesis of bis-chalcones based on 5,5΄-methylenebis(2-hydroxybenzaldehyde) and screening their antibacterial activity. Journal of Applied Chemistry, 9(32), 53-58.
• Teo, K. Y., Tiong, K. Y., Wee, H. Y., Jasin, N., Liu, Z. –Q., Shiu, M. Y., Tang, J. Y., Tsai, J. –K., Rahamathullah, R., Khariul, W. M., Tay, M. G. (2017). The influence of the push-pull effect and a π-conjugated system in conversion efficiency of bis-chalcone compounds in a dye sensitized solar cell. Journal of Molecular Structure, 1143, 42-48.
• Wei, Y., Qin, G., Wang, W., Bian, W., Shuang, S., Dong, C. (2011). Development of fluorescent FeIII sensor based on chalcone. Journal of Luminescence, 131(8), 1672-1676.
• Xu, J., Wang, C., Zhang, Q. (2001). Synthesis of 1,3,3a,5‐tetraaryl‐3a,4,5,6‐tetrahydro‐3H‐1,2,4‐triazolo[4,3‐a] [1,5] benzodiazepines. Heteroatom Chemistry, 6, 557-559.
• Yellepa, S., Mallapa, M. (2015). Electrochemical behavior of anticancer chalcone derivatives on glassy carbon electrode. European Journal of Pharmaceutical and Medical Research, 2(7), 146-150.
• Zhang, X. –W., Zhao, D. –H., Quan, Y. –C., Sun, L. –P., Yin X. –M., Guan L. –P. (2010). Synthesis and evaluation of antiinflammatory activity of substituted chalcone derivatives. Medicinal Chemistry Research, 19(4), 403-412.