Araştırma Makalesi
Yıl 2023,
Cilt: 9 Sayı: 1, 33 - 45, 21.06.2023
Öz
Destekleyen Kurum
Kastamonu Üniversitesi BAP Koordinatörlüğü
Proje Numarası
KÜ-BAP01/2017- 31
Kaynakça
- Anthony, R. P., Rodrigo, V.D., Louis, S.K., John, C.D., & Leroy, B.T. (1998). Design, synthesis, and antiviral evaluations of 1-(Substitutedbenzyl)-2-substituted-5,6 dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6-Trichloro-1-(b-D ribofuranosyl) benzimidazole. Journal of Medicinal Chemistry. 41(8), 1252-1262.
- Bansal, Y., & Silakari, O. (2012). The therapeutic journey of benzimidazoles: a review. Bioorganic & Medicinal Chemistry. 20(21), 6208-6236.
- Bishop, B.C., Chelton, E.T.J., & Jones, A.S. (1964). Biochemical Pharmacology. 13(5), 751-754.
- Habib, N.S., Soliman, R., Ashoura, F.A., & El-Taiebi, M. (1997). Synthesis and antimicrobial testing of novel oxadiazolylbenzimidazole derivatives. Die Pharmazie, 52(10), 746-749.
- Tuncbilek, M., Goker, H., Ertan, R., Eryigit, R., Kendi, E., & Altanlar, E. (1997). Synthesis and antimicrobial activity of some new anilino benzimidazoles. Archiv der Pharmazie, 330(12), 372-376.
- Göker, H., Tunçbilek, M., Süzen, S., Kus, C., & Altanlar, N. (2001). Synthesis and Antimicrobial Activity of Some New 2‐Phenyl‐N‐substituted Carboxamido‐1H‐benzimidazole Derivatives. Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry, 334(5), 148-152.
- Göker, H., Kuş, C., Boykin, D. W., Yildiz, S., & Altanlar, N. (2002). Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species. Bioorganic & medicinal chemistry, 10(8), 2589-2596.
- Pawar, N. S., Dalal, D. S., Shimpi, S. R., & Mahulikar, P. P. (2004). Studies of antimicrobial activity of N-alkyl and N-acyl 2-(4-thiazolyl)-1H-benzimidazoles. European journal of pharmaceutical sciences, 21(2-3), 115-118.
- Mohamed, B. G., Hussein, M. A., Abdel-Alim, A. A. M., & Hashem, M. (2006). Synthesis and antimicrobial activity of some new 1-alkyl-2-alkylthio-1, 2, 4-triazolobenzimidazole derivatives. Archives of pharmacal research, 29, 26-33.
- Vaidya, S. D., Kumar, B. V. S., Kumar, R. V., Bhise, U. N., & Mashelkar, U. C. (2007). Synthesis, anti‐bacterial, anti‐asthmatic and anti‐diabetic activities of novel N‐substituted‐2‐(benzo [d] isoxazol‐3‐ylmethyl)‐1H‐benzimidazoles. Journal of heterocyclic chemistry, 44(3), 685-691.
- Hogale, M. B., Uthale, A. C., & Nikam, B. P. (1991). hydrazidophenothiazines (IV). These intermediate inhibitory concentration (MIC) in mg/ml. The MIC. Indian Journal of Chemistry: Organic including medicinal. Section B, 30, 717-720.
- Srivastava, S. K., Srivastava, S., & Srivastava, S. D. (2002). Synthesis of new 1, 2, 4-triazolo-thiadiazoles and its 2-oxoazetidines as antimicrobial, anticonvulsant and antiinflammatory agents. Indian Journal of Chemistry. 41B, 2357-2363.
- Desai, K. G., & Desai, K. R. (2006). Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing–CONH–bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms. Bioorganic and medicinal chemistry, 14(24), 8271-8279.
- Furniss, B.S., Hannaford, A.J., Smith, P.W.G., & Tatchell, A.R. (Eds.) (1998). Vogel’s Text Book of Practical Organic Chemistry. ELBS Longman, England.
- Gür, M., Yerlikaya, S., Şener, N., Özkınalı, S., Baloglu, M. C., Gökçe, H., ... & Şener, İ. (2020). Antiproliferative-antimicrobial properties and structural analysis of newly synthesized Schiff bases derived from some 1, 3, 4-thiadiazole compounds. Journal of Molecular Structure, 1219, 128570.
- Ashour, F. A., Habib, N. S., El Taibbi, M., El Dine, S., & El Dine, A. S. (1990). Synthesis of 1, 3, 4-thiadiazoles, imidazo [2, 1-b] 1, 3, 4-thiadiazoles and thiadiazolo [3, 2-a] pyrimidines derived from benzimidazole as potential antimicrobial agents. Farmaco (Societa Chimica Italiana: 1989), 45(12), 1341-1349.
- Habib, N. S., Soliman, R., Ashour, F. A., & El-Taiebi, M. (1997). Synthesis and antimicrobial testing of 4H-1, 2, 4-triazole, 1, 2, 4-triazolo [3, 4-b][1, 3, 4] thiadiazole and 1, 2, 4-triazolo [3, 4-b][1, 3, 4] thiadiazine derivatives of 1H-benzimidazole. Die Pharmazie, 52(11), 844.
- Valeur, B., & Brochon, J. C. (Eds.). (2012). New trends in fluorescence spectroscopy: applications to chemical and life sciences (Vol. 1). Springer Science & Business Media.
- Strianese, M., Staiano, M., Ruggiero, G., Labella, T., Pellecchia, C., & D’Auria, S. (2012). Fluorescence-based biosensors. Spectroscopic methods of analysis: methods and protocols, 193-216.
- Goldys, E. M. (2009). Fluorescence applications in biotechnology and life sciences. John Wiley & Sons.
- Kraayenhof, R., Visser, A. J., & Gerritsen, H. C. (Eds.). (2012). Fluorescence spectroscopy, imaging and probes: new tools in chemical, physical and life sciences (Vol. 2). Springer Science & Business Media.
- Kalauzi, A., Mutavdžić, D., Djikanović, D., Radotić, K., & Jeremić, M. (2007). Application of asymmetric model in analysis of fluorescence spectra of biologically important molecules. Journal of fluorescence, 17(3), 319-329.
- Hunger, K. (Ed.). (2007). Industrial dyes: chemistry, properties, applications. John Wiley & Sons.
- Zollinger, H. (2003). Color chemistry: syntheses, properties, and applications of organic dyes and pigments. John Wiley & Sons.
- Kasture, P. P., Sonawane, Y. A., Rajule, R. N., & Shankarling, G. S. (2010). Synthesis and characterisation of benzothiazole‐based solid‐state fluorescent azo dyes. Coloration Technology, 126(6), 348-352.
- Ncube, P., Krause, R. W., & Mamba, B. B. (2011). Fluorescent sensing of chlorophenols in water using an azo dye modified β-cyclodextrin polymer. Sensors, 11(5), 4598-4608.
- Wolfbeis, O. S. (2005). Materials for fluorescence-based optical chemical sensors. Journal of Materials Chemistry, 15(27-28), 2657-2669.
- Lee, L. G., Taing, M. C., & Rosenblum, B. B. (2006). U.S. Patent No. 7,038,063. Washington, DC: U.S. Patent and Trademark Office.
- Chen, C. H., Liao, D. J., Wan, C. F., & Wu, A. T. (2013). A turn-on and reversible Schiff base fluorescence sensor for Al 3+ ion. Analyst, 138(9), 2527-2530.
- Hsieh, W. H., Wan, C. F., Liao, D. J., & Wu, A. T. (2012). A turn-on Schiff base fluorescence sensor for zinc ion. Tetrahedron letters, 53(44), 5848-5851.
- Guo, L., Wu, S., Zeng, F., & Zhao, J. (2006). Synthesis and fluorescence property of terbium complex with novel schiff-base macromolecular ligand. European polymer journal, 42(7), 1670-1675.
- Kohn, W., & Sham, L.J. (1965). Self-consistent equations including exchange and correlation effects. Physical Review. 140 (4A), 1133-1138.
- Hohenberg, P., & Kohn, W. (1964). Inhomogeneous Electron Gas, Physical Review. 136(3B), 864-871.
- Frisch, M., Trucks, G., & Schlegel, H. (2009). G.S.-G. 09, Gaussian, Inc., Wallingford CT.
- Bader, R. F. (1991). A quantum theory of molecular structure and its applications. Chemical Reviews, 91(5), 893-928.
- Bader, R. F. (1985). Atoms in molecules. Accounts of Chemical Research, 18(1), 9-15.
- Lu, T., & Chen, F. (2012). Multiwfn: A multifunctional wavefunction analyzer. Journal of computational chemistry, 33(5), 580-592.
- Aydogdu, S., & Hatipoglu, A. (2022). The reaction mechanism investigation of sulfonamides with OH radical by DFT. Journal of the Indian Chemical Society, 99(11), 100752.
- Domingo, L. R., & Pérez, P. (2011). The nucleophilicity N index in organic chemistry. Organic & biomolecular chemistry, 9(20), 7168-7175.
Comparison of Absorption-Emission Properties of New Azo Dyes and New Schiff Bases from Benzimidazole Derivative 1,3,4-Thiadiazole and Theoretical Calculation by DFT Method
Öz
After the synthesis of the new benzimidazole derivative 1,3,4-thiadiazole compound, a series of azo dyes from the reaction of this compound with various coupling components and a series of schiff bases were synthesized from the reaction with various aldehydes. The structures of the obtained compounds are characterized and interpreted with UV, FT-IR and 1H-NMR. The fluorescence properties of the compounds were also investigated, and the absorption and emission properties of schiff base and azo dyes obtained from the same derivative were examined. As a result, it was observed that schiff bases obtained from benzimidazole derivative 1,3,4-thiadiazole compound had longer wavelength absorption-emission compared to azo dyes obtained from the same compound. Experimental data were supported by density functional theory (DFT) calculations. The ground state geometries, spectroscopic properties, FMO energies and related chemical reactivity parameters of the compounds were calculated using the B3LYP hybrid density functional combined with 6-311++G(2d,2p) basis set. At the same theory level, QTAIM and IRI analyzes were also performed and the data were used to determine the properties of tautomeric structures. The electronic properties of the compounds were studied and a detailed analysis was performed by comparing them with experimental data.
Anahtar Kelimeler
Benzimidazole Azo dyes Schiff bases Fluorescence Absorption properties DFT method
Proje Numarası
KÜ-BAP01/2017- 31
Kaynakça
- Anthony, R. P., Rodrigo, V.D., Louis, S.K., John, C.D., & Leroy, B.T. (1998). Design, synthesis, and antiviral evaluations of 1-(Substitutedbenzyl)-2-substituted-5,6 dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6-Trichloro-1-(b-D ribofuranosyl) benzimidazole. Journal of Medicinal Chemistry. 41(8), 1252-1262.
- Bansal, Y., & Silakari, O. (2012). The therapeutic journey of benzimidazoles: a review. Bioorganic & Medicinal Chemistry. 20(21), 6208-6236.
- Bishop, B.C., Chelton, E.T.J., & Jones, A.S. (1964). Biochemical Pharmacology. 13(5), 751-754.
- Habib, N.S., Soliman, R., Ashoura, F.A., & El-Taiebi, M. (1997). Synthesis and antimicrobial testing of novel oxadiazolylbenzimidazole derivatives. Die Pharmazie, 52(10), 746-749.
- Tuncbilek, M., Goker, H., Ertan, R., Eryigit, R., Kendi, E., & Altanlar, E. (1997). Synthesis and antimicrobial activity of some new anilino benzimidazoles. Archiv der Pharmazie, 330(12), 372-376.
- Göker, H., Tunçbilek, M., Süzen, S., Kus, C., & Altanlar, N. (2001). Synthesis and Antimicrobial Activity of Some New 2‐Phenyl‐N‐substituted Carboxamido‐1H‐benzimidazole Derivatives. Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry, 334(5), 148-152.
- Göker, H., Kuş, C., Boykin, D. W., Yildiz, S., & Altanlar, N. (2002). Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species. Bioorganic & medicinal chemistry, 10(8), 2589-2596.
- Pawar, N. S., Dalal, D. S., Shimpi, S. R., & Mahulikar, P. P. (2004). Studies of antimicrobial activity of N-alkyl and N-acyl 2-(4-thiazolyl)-1H-benzimidazoles. European journal of pharmaceutical sciences, 21(2-3), 115-118.
- Mohamed, B. G., Hussein, M. A., Abdel-Alim, A. A. M., & Hashem, M. (2006). Synthesis and antimicrobial activity of some new 1-alkyl-2-alkylthio-1, 2, 4-triazolobenzimidazole derivatives. Archives of pharmacal research, 29, 26-33.
- Vaidya, S. D., Kumar, B. V. S., Kumar, R. V., Bhise, U. N., & Mashelkar, U. C. (2007). Synthesis, anti‐bacterial, anti‐asthmatic and anti‐diabetic activities of novel N‐substituted‐2‐(benzo [d] isoxazol‐3‐ylmethyl)‐1H‐benzimidazoles. Journal of heterocyclic chemistry, 44(3), 685-691.
- Hogale, M. B., Uthale, A. C., & Nikam, B. P. (1991). hydrazidophenothiazines (IV). These intermediate inhibitory concentration (MIC) in mg/ml. The MIC. Indian Journal of Chemistry: Organic including medicinal. Section B, 30, 717-720.
- Srivastava, S. K., Srivastava, S., & Srivastava, S. D. (2002). Synthesis of new 1, 2, 4-triazolo-thiadiazoles and its 2-oxoazetidines as antimicrobial, anticonvulsant and antiinflammatory agents. Indian Journal of Chemistry. 41B, 2357-2363.
- Desai, K. G., & Desai, K. R. (2006). Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing–CONH–bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms. Bioorganic and medicinal chemistry, 14(24), 8271-8279.
- Furniss, B.S., Hannaford, A.J., Smith, P.W.G., & Tatchell, A.R. (Eds.) (1998). Vogel’s Text Book of Practical Organic Chemistry. ELBS Longman, England.
- Gür, M., Yerlikaya, S., Şener, N., Özkınalı, S., Baloglu, M. C., Gökçe, H., ... & Şener, İ. (2020). Antiproliferative-antimicrobial properties and structural analysis of newly synthesized Schiff bases derived from some 1, 3, 4-thiadiazole compounds. Journal of Molecular Structure, 1219, 128570.
- Ashour, F. A., Habib, N. S., El Taibbi, M., El Dine, S., & El Dine, A. S. (1990). Synthesis of 1, 3, 4-thiadiazoles, imidazo [2, 1-b] 1, 3, 4-thiadiazoles and thiadiazolo [3, 2-a] pyrimidines derived from benzimidazole as potential antimicrobial agents. Farmaco (Societa Chimica Italiana: 1989), 45(12), 1341-1349.
- Habib, N. S., Soliman, R., Ashour, F. A., & El-Taiebi, M. (1997). Synthesis and antimicrobial testing of 4H-1, 2, 4-triazole, 1, 2, 4-triazolo [3, 4-b][1, 3, 4] thiadiazole and 1, 2, 4-triazolo [3, 4-b][1, 3, 4] thiadiazine derivatives of 1H-benzimidazole. Die Pharmazie, 52(11), 844.
- Valeur, B., & Brochon, J. C. (Eds.). (2012). New trends in fluorescence spectroscopy: applications to chemical and life sciences (Vol. 1). Springer Science & Business Media.
- Strianese, M., Staiano, M., Ruggiero, G., Labella, T., Pellecchia, C., & D’Auria, S. (2012). Fluorescence-based biosensors. Spectroscopic methods of analysis: methods and protocols, 193-216.
- Goldys, E. M. (2009). Fluorescence applications in biotechnology and life sciences. John Wiley & Sons.
- Kraayenhof, R., Visser, A. J., & Gerritsen, H. C. (Eds.). (2012). Fluorescence spectroscopy, imaging and probes: new tools in chemical, physical and life sciences (Vol. 2). Springer Science & Business Media.
- Kalauzi, A., Mutavdžić, D., Djikanović, D., Radotić, K., & Jeremić, M. (2007). Application of asymmetric model in analysis of fluorescence spectra of biologically important molecules. Journal of fluorescence, 17(3), 319-329.
- Hunger, K. (Ed.). (2007). Industrial dyes: chemistry, properties, applications. John Wiley & Sons.
- Zollinger, H. (2003). Color chemistry: syntheses, properties, and applications of organic dyes and pigments. John Wiley & Sons.
- Kasture, P. P., Sonawane, Y. A., Rajule, R. N., & Shankarling, G. S. (2010). Synthesis and characterisation of benzothiazole‐based solid‐state fluorescent azo dyes. Coloration Technology, 126(6), 348-352.
- Ncube, P., Krause, R. W., & Mamba, B. B. (2011). Fluorescent sensing of chlorophenols in water using an azo dye modified β-cyclodextrin polymer. Sensors, 11(5), 4598-4608.
- Wolfbeis, O. S. (2005). Materials for fluorescence-based optical chemical sensors. Journal of Materials Chemistry, 15(27-28), 2657-2669.
- Lee, L. G., Taing, M. C., & Rosenblum, B. B. (2006). U.S. Patent No. 7,038,063. Washington, DC: U.S. Patent and Trademark Office.
- Chen, C. H., Liao, D. J., Wan, C. F., & Wu, A. T. (2013). A turn-on and reversible Schiff base fluorescence sensor for Al 3+ ion. Analyst, 138(9), 2527-2530.
- Hsieh, W. H., Wan, C. F., Liao, D. J., & Wu, A. T. (2012). A turn-on Schiff base fluorescence sensor for zinc ion. Tetrahedron letters, 53(44), 5848-5851.
- Guo, L., Wu, S., Zeng, F., & Zhao, J. (2006). Synthesis and fluorescence property of terbium complex with novel schiff-base macromolecular ligand. European polymer journal, 42(7), 1670-1675.
- Kohn, W., & Sham, L.J. (1965). Self-consistent equations including exchange and correlation effects. Physical Review. 140 (4A), 1133-1138.
- Hohenberg, P., & Kohn, W. (1964). Inhomogeneous Electron Gas, Physical Review. 136(3B), 864-871.
- Frisch, M., Trucks, G., & Schlegel, H. (2009). G.S.-G. 09, Gaussian, Inc., Wallingford CT.
- Bader, R. F. (1991). A quantum theory of molecular structure and its applications. Chemical Reviews, 91(5), 893-928.
- Bader, R. F. (1985). Atoms in molecules. Accounts of Chemical Research, 18(1), 9-15.
- Lu, T., & Chen, F. (2012). Multiwfn: A multifunctional wavefunction analyzer. Journal of computational chemistry, 33(5), 580-592.
- Aydogdu, S., & Hatipoglu, A. (2022). The reaction mechanism investigation of sulfonamides with OH radical by DFT. Journal of the Indian Chemical Society, 99(11), 100752.
- Domingo, L. R., & Pérez, P. (2011). The nucleophilicity N index in organic chemistry. Organic & biomolecular chemistry, 9(20), 7168-7175.
Toplam 39 adet kaynakça vardır.
Ayrıntılar
| Birincil Dil | İngilizce |
|---|---|
| Konular | Mühendislik |
| Bölüm | Araştırma Makalesi |
| Yazarlar | |
| Proje Numarası | KÜ-BAP01/2017- 31 |
| Erken Görünüm Tarihi | 20 Haziran 2023 |
| Yayımlanma Tarihi | 21 Haziran 2023 |
| Gönderilme Tarihi | 23 Mayıs 2023 |
| Yayımlandığı Sayı | Yıl 2023 Cilt: 9 Sayı: 1 |
Kaynak Göster
