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Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings

Yıl 2025, Erken Görünüm, 1 - 1
https://doi.org/10.35378/gujs.1422427

Öz

New azo dyes (1a-b) were produced by the azo coupling of 2-nitro-1,4-phenylenediamine with 5-chlorosalicylaldehyde and 5-chloro-2-hydroxyaniline. Corresponding Schiff base derivatives (2a-b) bearing conjugated benzimidazole and imidazole moieties were obtained via the condensation reaction of these dyes with 2-aminobenzimidazole and 4-imidazolecarboxaldehyde. Their structures were identified by IR, 1H/13C NMR, mass and UV–Vis spectroscopies and microanalysis. Chromic (solvato-, acido-, thermo-) and photoluminescence behaviour of compounds 2a and 2b were evaluated depending on their donor–π–acceptor molecular system and intramolecular proton tautomerism. Electronic absorption and photoluminescence spectra of 2a and 2b were recorded in DMSO, DMF and CHCl3. 2a emitted turquoise luminescence in DMSO and DMF, and white luminescence in CHCl3, while 2b emitted strong turquoise luminescence in only CHCl3.

Destekleyen Kurum

Research Foundation of Gazi University

Proje Numarası

F.E.F. 05/2019–23

Teşekkür

I am thankful to Research Foundation of Gazi University (Project ID: F.E.F. 05/2019–23). I am also grateful to Photonics Application and Research Center of Gazi University for photoluminescence measurements.

Kaynakça

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Yıl 2025, Erken Görünüm, 1 - 1
https://doi.org/10.35378/gujs.1422427

Öz

Proje Numarası

F.E.F. 05/2019–23

Kaynakça

  • [1] Fita, P., Luzina, E., Dziembowska, T., Kopec, D., Piatkowski, P., Radzewicz, Cz., Grabowska, A., “Keto–enol tautomerism of two structurally related Schiff bases: Direct and indirect way of creation of the excited keto tautomer”, Chemical Physics Letters, 416: 305–310, (2005).
  • [2] Meng, X., Zhu, W., Zhang, Q., Feng, Y., Tan, W., Tian, H., “Novel bisthienylethenes containing naphthalimide as the center ethene bridge: photochromism and solvatochromism for combined nor and inhibit logic gates”, The Journal of Physical Chemistry B, 112: 15636–15645, (2008).
  • [3] Atav, R., Topuz, A., Arıcan, T., “Köpüklü aplikasyon tekniği kullanılarak UV ile renk değiştiren fonksiyonel floklu döşemelik kumaş geliştirilmesi”, European Journal of Engineering and Applied Sciences, 1: 15–18, (2018).
  • [4] Pakolpakçıl, A., Karaca, E., Becerir, B., “Halokromik akıllı tekstil yüzeyleri ve tıbbi amaçlı kullanım olanakları”, Journal of Textile Engineering, 25(111): 214–224, (2018).
  • [5] Açıksarı, C., Karasu, B., “Smart glasses and their technological developments”, The El-Cezerî Journal of Science and Engineering, 5(2): 437–457, (2018).
  • [6] Eren, Z., Acar, F.N., “Uçucu kül adsorpsiyonu ile reaktif boya giderimi”, Pamukkale University Journal of Engineering Sciences, 10(2): 253–258, (2004).
  • [7] Sener, N., Sener, I., Yavuz, S., Karcı, F., “Synthesis, absorption properties and biological evaluation of some novel disazo dyes derived form pyrazole derivatives”, Asian Journal of Chemistry, 27: 3003–3012, (2015).
  • [8] Sheikhshoaie, I., Hossein, M., Mashhadizadeh, Saeid-Nia, S., “Synthesis, characterization and theoretical study of the structure and second-order nonlinear optical properties of two new monoazo Schiff-base compounds”, Journal of Coordination Chemistry, 57(5): 417–423, (2004). [9] Coelho, P.J., Carvalho, L.M., Fonseca, A.M.C., Raposo, M. M. M., “Photochromic properties of thienylpyrrole azo dyes in solution”, Tetrahedron Letters, 47: 3711–3714, (2006).
  • [10] Yılmaz, Z.K., Özdemir, Ö., Aslim, B., Suludere, Z., Şahin, E., “A new bio-active asymmetric-Schiff base: synthesis and evaluation of calf thymus DNA interaction, topoisomerase IIα inhibition, in vitro antiproliferative activity, SEM analysis and molecular docking studies”, Journal of Biomolecular Structure and Dynamics, 41: 2804–2822, (2023).
  • [11] Abdel Aziz, A.A., Badr, I.H.A., El-Sayed, I.S.A., “Synthesis, spectroscopic, photoluminescence properties and biological evaluation of novel Zn(II) and Al(III) complexes of NOON tetradentate Schiff bases”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97: 388–396, (2012).
  • [12] Raman, N., Selvan, A., Sudharsan, S., “Metallation of ethylenediamine based Schiff base with biologically active Cu(II), Ni(II) and Zn(II) ions: synthesis, spectroscopic characterization, electrochemical behaviour, DNA binding, photonuclease activity and invitro antimicrobial efficacy”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79: 873–883, (2011).
  • [13] Nagaveni, V.B., Mahadevan, K.M., Vijayakumar, G.R., Nagabhushana, H., Naveen, S., Lokanath, N.K., “Synthesis, crystal structure and excellent photoluminescence properties of copper (II) and cobalt (II) complexes with Bis(1[(4-butylphenyl)imino]methyl naphthalen-2-ol) Schiff base”, Journal of Science: Advanced Materials and Devices, 3: 51–58, (2018).
  • [14] Zhang, J., Xu, L., Wong, W.Y., “Energy materials based on metal Schiff base complexes”, Coordination Chemistry Reviews, 355: 180–198, (2018).
  • [15] Özkınalı, S., Gür, M., Şener, N., Alkın, S., Çavuş, M.S., “Synthesis of new azo schiff bases of pyrazole derivatives and their spectroscopic and theoretical investigations”, Journal of Molecular Structure, 1174: 74–83, (2018).
  • [16] Anitha, C., Sheela, C.D., Tharmaraj, P., Sumathi, S., “Spectroscopic studies and biological evaluation of some transition metal complexes of azo Schiff-base ligand derived from (1-phenyl-2,3-dimethyl-4-aminopyrazol-5-one) and 5-((4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 96: 493–500, (2012).
  • [17] Mallikarjuna, N.M., Keshavayya, J., Maliyappa, M.R., Shoukat Ali, R.A., Venkatesh, T., “Synthesis, characterization, thermal and biological evaluation of Cu(II), Co(II) and Ni(II) complexes of azo dye ligand containing sulfamethaxazole moiety”, Journal of Molecular Structure, 1165: 28–36, (2018).
  • [18] Kakanejadifard, A., Azarbani, F., Zabardasti, A., Kakanejadifard, S., Ghasemian, M., Esna-ashari, F., Omidi, S., Shirali, S., Rafieefar, M., “The synthesis, structural characterization and antibacterial properties of some 2-((4-amino-1,2,5-oxadiazol-3-ylimino)methyl)-4-(phenyldiazenyl)phenol”, Dyes and Pigments, 97: 215–221, (2013).
  • [19] Bal, S., Connolly, J.D., “Synthesis, characterization, thermal and catalytic properties of a novel carbazole derived azo ligand and its metal complexes”, Arabian Journal of Chemistry, 10: 761–768, (2017).
  • [20] Slassi, S., Fix-Tailler, A., Larcher, G., Amine, A., El-Ghayoury, A., “Imidazole and azo-based Schiff bases ligands as highly active antifungal and antioxidant components”, Heteroatom Chemistry, 2019: 6862170, (2019).
  • [21] Dutta, P., Mallick, D., Roy, S., Torres, E.L., Sinha, C., “Dihalo-bis[1-alkyl-2-{(o-thioalkyl)phenylazo}imidazole]zinc(II): structure, photochromism and DFT computation”, Inorganica Chimica Acta, 423: 397–407, (2014).
  • [22] Khedr, A.M., Gaber, M., Issa, R.M., Erten, H., “Synthesis and spectral studies of 5-[3-(1,2,4-triazolyl-azo]-2,4-dihydroxybenzaldehyde (TA) and its Schiff bases with 1,3-diaminopropane (TAAP) and 1,6-diaminohexane (TAAH). Their analytical application for spectrophotometric microdetermination of cobalt(II). Application in some radiochemical studies”, Dyes and Pigments, 67: 117–126, (2005).
  • [23] Pervaiz, M., Sadiq, S., Sadiq, A., Younas, U., Ashraf, A., Saeed, Z., Zuber, M., Adnan, A., “Azo-Schiff base derivatives of transition metal complexes as antimicrobial agents”, Coordination Chemistry Reviews, 447: 214128, (2021).
  • [24] Venugopal, N., Krishnamurthy, G., Bhojyanaik, H.S., Giridhar, M., “Novel bioactive azo-azomethine based Cu(II), Co(II) and Ni(II) complexes, structural determination and biological activity”, Journal of Molecular Structure, 1191: 85–94, (2019).
  • [25] Tawfik, A.M., El-ghamry, M.A., Abu-El-Wafa, S.M., Ahmed, N.M., “A new bioactive Schiff base ligands derived from propylazo-N-pyrimidin-2-yl-benzenesulfonamides Mn(II) and Cu(II) complexes: Synthesis, thermal and spectroscopic characterization biological studies and 3D modeling structures”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97: 1172–1180, (2012).
  • [26] Anitha, C., Sheela, C.D., Tharmaraj, P., Johnson Raja, S., “Synthesis and characterization of VO(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes of chromone based azo-linked Schiff base ligand”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 98: 35–42, (2012).
  • [27] Dinçalp, H., Yavuz, S., Haklı, Ö., Zafer, C., Özsoy, C., Durucasu, İ., İçli, S., “Optical and photovoltaic properties of salicylaldimine-based azo ligands”, Journal of Photochemistry and Photobiology A: Chemistry, 210: 8–16, (2010).
  • [28] Mahmoodi, N.O., Nadamani, M.P., Behzadi, T., “New 1,3-diazabicyclo-[3.1.0]hex-3-ene photochromic azo dyes: Synthesis, characterization and spectroscopic studies”, Journal of Molecular Liquids, 187: 43–48, (2013).
  • [29] Gilani, A.G., Taghvaei, V., Rufchahi, E.M., Mirzaei, M., “Tautomerism, solvatochromism, preferential solvation, and density functional study of some heteroarylazo dyes”, Journal of Molecular Liquids, 273: 392–407, (2019).
  • [30] Ajaj, I., Assaleh, F.H., Markovski, J., Rancic, M., Brkovic, D., Milcic, M., Marinkovic, A.D., “Solvatochromism and azo–hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study”, Arabian Journal of Chemistry, 12: 3463-3478, (2015).
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  • [32] Dhaka, G., Kaur, N., Singh, J., “Spectral studies on benzimidazole-based ‘‘bare-eye” probe for the detection of Ni2+: Application as a solid state sensor”, Inorganica Chimica Acta, 464: 18–22, (2017).
  • [33] Sondhi, S.M., Singh, N., Kumar, A., Lozach, O., Meijer, L., “Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff’s bases”, Bioorganic and Medicinal Chemistry, 14: 3758–3765, (2006).
  • [34] Mahmoodi, N.O., Rahimi, S., Nadamani, M.P., “Microwave-assisted synthesis and photochromic properties of new azo-imidazoles”, Dyes and Pigments, 143: 387–392, (2017).
  • [35] Khungar, B., Rao, M.S., Pericherla, K., Nehra, P., Jain, N., Panwar, J., Kumar, A., “Synthesis, characterization and microbiocidal studies of novel ionic liquid tagged Schiff bases”, Comptes Rendus Chimie, 15: 669-674, (2012).
  • [36] Kumaravel, G., Raman, N., “A treatise on benzimidazole based Schiff base metal(II) complexes accentuating their biological efficacy: Spectroscopic evaluation of DNA interactions, DNA cleavage and antimicrobial screening”, Materials Science and Engineering: C, 70: 184–194, (2017).
  • [37] Wang, X., Xu, T., Duan, H., “Schiff base fluorescence probes for Cu2+ based on imidazole and benzimidazole”, Sensors and Actuators B: Chemical, 214: 138–143, (2015).
  • [38] Özdemir, Ö., “Synthesis of novel azo linkage-based Schiff bases including anthranilic acid and hexanoic acid moieties: investigation of azo-hydrazone and phenol-keto tautomerism, solvatochromism, and ionochromism”, Turkish Journal of Chemistry, 43: 266–285, (2019)
  • [39] Joseph, J., Suman, A., Nagashri, K., Joseyphus, R.S., Balakrishnan, N., “Synthesis, characterization and biological studies of copper(II) complexes with 2-aminobenzimidazole derivatives“, Journal of Molecular Structure, 1137: 17–26, (2017).
  • [40] Kalarani, R., Sankarganesh, M., Vinoth, Kumar, G.G., Kalanithi, M., “Synthesis, spectral, DFT calculation, sensor, antimicrobial and DNA binding studies of Co(II), Cu(II) and Zn(II) metal complexes with 2-amino benzimidazole Schiff base”, Journal of Molecular Structure, 1206: 127725, (2020).
  • [41] Zarei, S.A., “A mononuclear cobalt(II) salophen-type complex: Synthesis, theoretical and experimental electronic absorption and infrared spectra, crystal structure, and predicting of second- and third-order nonlinear optical properties”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 215: 225–232, (2019).
  • [42] Kumaravel, G., Utthra, P.P., Raman, N., “Exploiting the biological efficacy of benzimidazole based Schiff base complexes with L-Histidine as a co-ligand: Combined molecular docking, DNA interaction, antimicrobial and cytotoxic studies”, Bioorganic Chemistry, 77: 269–279, (2018).
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  • [51] Zhao, X.L., Geng, J., Qian, H.F., Huang, W., “pH-induced azo-keto and azo-enol tautomerism for 6-(3-methoxypropylamino)pyridin-2-one based thiophene azo dyes”, Dyes and Pigments, 147: 318–326, (2017).
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Toplam 56 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular İnorganik Kimya (Diğer), Organik Kimyasal Sentez
Bölüm Research Article
Yazarlar

Özlem Güngör 0000-0003-2748-9179

Proje Numarası F.E.F. 05/2019–23
Erken Görünüm Tarihi 27 Ekim 2024
Yayımlanma Tarihi
Gönderilme Tarihi 19 Ocak 2024
Kabul Tarihi 3 Temmuz 2024
Yayımlandığı Sayı Yıl 2025 Erken Görünüm

Kaynak Göster

APA Güngör, Ö. (2024). Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings. Gazi University Journal of Science1-1. https://doi.org/10.35378/gujs.1422427
AMA Güngör Ö. Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings. Gazi University Journal of Science. Published online 01 Ekim 2024:1-1. doi:10.35378/gujs.1422427
Chicago Güngör, Özlem. “Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings”. Gazi University Journal of Science, Ekim (Ekim 2024), 1-1. https://doi.org/10.35378/gujs.1422427.
EndNote Güngör Ö (01 Ekim 2024) Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings. Gazi University Journal of Science 1–1.
IEEE Ö. Güngör, “Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings”, Gazi University Journal of Science, ss. 1–1, Ekim 2024, doi: 10.35378/gujs.1422427.
ISNAD Güngör, Özlem. “Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings”. Gazi University Journal of Science. Ekim 2024. 1-1. https://doi.org/10.35378/gujs.1422427.
JAMA Güngör Ö. Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings. Gazi University Journal of Science. 2024;:1–1.
MLA Güngör, Özlem. “Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings”. Gazi University Journal of Science, 2024, ss. 1-1, doi:10.35378/gujs.1422427.
Vancouver Güngör Ö. Fabricating of Turquoise/White Luminescent Azo-Schiff Bases Bearing Benzimidazole and Imidazole Rings. Gazi University Journal of Science. 2024:1-.