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

Year 2025, Early View, 1 - 1

Özlem Güngör

https://doi.org/10.35378/gujs.1422427

Abstract

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.

Keywords

Azo-Schiff bases Benzimidazole Imidazole Turquoise luminescence White luminescence

Supporting Institution

Research Foundation of Gazi University

Project Number

F.E.F. 05/2019–23

Thanks

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.

References

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Year 2025, Early View, 1 - 1

Özlem Güngör

https://doi.org/10.35378/gujs.1422427

Abstract

Project Number

F.E.F. 05/2019–23

References

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  • [6] Eren, Z., Acar, F.N., “Uçucu kül adsorpsiyonu ile reaktif boya giderimi”, Pamukkale University Journal of Engineering Sciences, 10(2): 253–258, (2004).
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  • [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).
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There are 56 citations in total.

Details

Primary Language English
Subjects Inorganic Chemistry (Other), Organic Chemical Synthesis
Journal Section Research Article
Authors

Özlem Güngör 0000-0003-2748-9179

Project Number F.E.F. 05/2019–23
Early Pub Date October 27, 2024
Publication Date
Submission Date January 19, 2024
Acceptance Date July 3, 2024
Published in Issue Year 2025 Early View

Cite

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 October 1, 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, October (October 2024), 1-1. https://doi.org/10.35378/gujs.1422427.
EndNote Güngör Ö (October 1, 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, pp. 1–1, October 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. October 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, pp. 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-.