Yıl: 2018 Cilt: 5 Sayı: 3 Sayfa Aralığı: 1375 - 1386 Metin Dili: İngilizce DOI: 10.18596/jotcsa.478665 İndeks Tarihi: 29-02-2020

Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study

Öz:
In this study, we synthesized a novel benzimidazole-based Schiff base; (E)-4,4'-methylenebis(2-((E)-(((1H-benzo[d]imidazol-2-yl)methyl)imino)methyl)phenol) (3) was synthesized bythe condensation of 5,5'-methylenebis(2-hydroxybenzaldehyde) (1) and (1H-benzo[d]imidazol-2-yl)methanamine.HCl salt (2). This Schiff base derivative was reported for the first time and fullycharacterized by common spectroscopic techniques. Absorption and fluorescence spectroscopy wererecorded to determine the sensing ability of 3 towards metal ions. Selectivity to Zn2+ ion among studiedother cations was detected. The crystal structure of 2, C8H13Cl2N3O, has been determined by single crystalX-ray diffraction method. The crystal structure of the title compound, $C8H11N32+2(Cl-)H2O$, consists of anorganic 1H-benzoimidazol-3-ium (C8H11N32+) cation, an inorganic 2(Cl-) anion and one water (H2O)molecule. In the cation of studied compound, C8H11N32+, the benzimidazole ring is almost planar with amaximum deviation of -0.012 (3) Å. The molecule crystallized in the monoclinic structure and the spacegroup P21/c. The crystalline stacking structure is stabilized by intramolecular N–H···Cl, N–H···O, theintermolecular N–H···Cl hydrogen bond interactions connection the molecules into a two dimensionalnetwork and between anions and the water molecules. π-π interaction between benzimidazole rings[centroid–centroid lengths = 3.4642 (2) Å, 3.5309 (2) Å and 3.5527 (2) Å] may further stabilize thestructure.
Anahtar Kelime:

Konular: Kimya, Analitik Termodinamik Spektroskopi Kimya, Uygulamalı Kimya, Organik Kimya, Tıbbi Fizikokimya Kimya, İnorganik ve Nükleer
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • 1. Preston PN. Chemistry of Heterocyclic Compounds: Benzimidazoles and Cogeneric Tricyclic Compounds. John Wiley&Sons, Inc, New York; 2008
  • 2. El Rashedy AA, Aboul-Enein HY. Benzimidazole derivatives as potential anticancer agents. Mini-Rev. Med. Chem. 2013;13:399-407.
  • 3. El-masry AH, Fahmy HH, Abdelwahed SH. Synthesis and Antimicrobial Activity of Some New Benzimidazole Derivatives. Molecules. 2000;5:1429-38.
  • 4. Gaba M, Singh S, Mohan C. Benzimidazole: An emerging scaffold for analgesic and antiinflammatory agents. Eur. J. Med. Chem. 2014;76:494-505.
  • 5. Patil A, Ganguly S, Surana S. A systematic Review of benzimidazole Derivatives as an Antiulcer Agent. Rasayan J Chem. 2008;1:447-60.
  • 6. Kus C, Kilcgil AG, Eke BC, Iscan M. Synthesis and antioxidant properties of some novel benzimidazole derivatives on lipid peroxidation in the rat liver. Arch Pharm. Res. 2004;27:156-63.
  • 7. Kathiravan MK, Salake AB, Chothe AS, Dudhe PB, Wat RP. The biology and chemistry of antifungal agents: A review. Bioorg Med. Chem. 2012;20:5678–98.
  • 8. Cetinkaya B, Özdemir I, Bruneau C, Dixneuf PH. Benzimidazole, Benzothiazole and Benzoxazole Ruthenium(II) Complexes; Catalytic Synthesis of 2,3-Dimethylfuran. Eur J Inorg. Chem. 2000;2000:29-32.
  • 9. Tong Y, Zheng S, Chen X. Structures, Photoluminescence and Theoretical Studies of Two ZnII Complexes with Substituted 2-(2-Hydroxyphenyl)benzimidazoles. Eur J Inorg Chem. 2005;2005:3734–41.
  • 10. Verdasco G, Martin MA, Castillo B, Lopez- Alvarado P, Menendez JC. Solvent effects on the fluorescent emission of some new benzimidazole derivatives. Anal Chim Acta. 1995;303:73-8.
  • 11. Arulmurugan S, Kavitha HP, Venkatraman BR. Biological Activities of Schiff Bae and Its Complexes: A Review. Rasayan J Chem. 2010;3: 385-410.
  • 12. Przybylski P, Huczynski A, Pyta K, Brzezinski B, Bartl F. Biological Properties of Schiff Bases and Azo Derivatives of Phenols. Curr Org. Chem. 2009;13:124-48.
  • 13. Wang L, Qin W, Liu W. A sensitive Schiffbase fluorescent indicator for the detection of Zn2+. Inorg Chem Commun. 2010;13:1122– 25.
  • 14. Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE, Signaling Recognition Events with Fluorescent Sensors and Switches. Chem Rev. 1997;97:1515–66.
  • 15. Carter KP, Young AM, Palmer AE. Fluorescent Sensors for Measuring Metal Ions in Living Systems Chem Rev. 2014;114: 4564−4601.
  • 16. Singh N, Jang DO. Benzimidazole-Based Tripodal Receptor: Highly Selective Fluorescent Chemosensor for Iodide in Aqueous Solution. Org Lett. 2007;9:1991-4.
  • 17. Lee DY, Singh N, Jang DO. A benzimidazole-based single molecular multianalyte fluorescent probe for the simultaneous analysis of Cu2+ and Fe3+. Tetrahedron Lett. 2010;51:1103–6.
  • 18. Lin H, Cheng P, Wanb C, Wu A, A turn-on and reversible fluorescence sensor for zinc ion. Analyst. 2012;137: 4415-7.
  • 19. Auld DS. Zinc coordination sphere in biochemical zinc sites. BioMetals. 2001;14:271.
  • 20. Perrin DD, Armarego WLF, Perrin DR. Purification of Laboratory Chemicals. Pergamon Press, New York:2013.
  • 21. Lin CH, Feng YR, Dai KH, Chang HC, Juang TY. Synthesis of a benzoxazine with precisely two phenolic OH linkages and the properties of its high-performance copolymers. J Polym Sci Part A: Polym Chem. 2013;51:2686-94.
  • 22. Alasmary FAS, Snelling AM, Zain ME, Alafeefy AM, Awaad AS, Karodia N. Molecules. 2015;20:15206-23.
  • 23. STOE & Cie, X-AREA (Version 1.18) and XRED32 (Version 1.04), STOE & Cie, Darmstadt, Germany;2002.
  • 24. Sheldrick GM. A short history of SHELX. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008;64:112-122.
  • 25. Farrugia LJ. ORTEP-3 for Windows- a version of ORTEP-III with a Graphical User Interface (GUI). J Appl Crystallogr. 1997;30:565.
  • 26. Spek AL. Structure validation in chemical crystallography. Acta Crystallogr. 2009;D65:148-55.
  • 27. Farrugia LJ. WinGX and ORTEP for Windows: an update. J Appl Crystallogr. 1999;32:837-838.
  • 28. Özçelik S, Gül A. Boronic ester of a phthalocyanine precursor with a salicylaldimino moiety. J Organomet. Chem. 2012;699:87-91.
  • 29. Zheng S, Cai Y, Zhanga X, Sua C. 2,2'- (Iminodimethylene)bis(1Hbenzimidazolium)( 1+) chloride. Acta Cryst. 2005;E61:642-4.
  • 30. Cui Y. 2,2’,2’’- (Nitrilotrimethylene)tris(1Hbenzimidazol-3- ium) trinitrate. Acta Cryst. 2011;E67:625-6.
  • 31. Li G, Yang F, Yao C. 2-Amino-1Hbenzoimidazol- 3-ium 4,4,4- trifluoro-1,3- dioxo-1-phenylbutan-2-ide. Acta Cryst. 2008;E64:2460.
  • 32. Jana A, Sukul PK, Mandal SK, Konar S, Ray S, Das K, et al. A novel 2,6-diformyl-4- methylphenol based chemosensor for Zn(II) ions by ratiometric displacement of Cd(II) ions and its application for cell imaging on human melanoma cancer cells. Analyst, 2014;139:495–504.
  • 33. Sen P, Atmaca GY, Erdogmus A, Dege N, Genc H, Atalay Y, Yildiz SZ. The Synthesis, Characterization, Crystal Structure and Photophysical Properties of a New Meso- BODIPY Substituted Phthalonitrile. J Fluoresc. 2015;25:1225-34.
  • 34. Brouwer AM. Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report). Pure Appl Chem. 2011;83:2213-28.
APA Şen P, YILDIZ S, Dege N, YAŞA ATMACA G, ERDOGMUS A, DEGE M (2018). Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. , 1375 - 1386. 10.18596/jotcsa.478665
Chicago Şen Pınar,YILDIZ Salih Zeki,Dege Necmi,YAŞA ATMACA Göknur,ERDOGMUS ALI,DEGE Mustafa Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. (2018): 1375 - 1386. 10.18596/jotcsa.478665
MLA Şen Pınar,YILDIZ Salih Zeki,Dege Necmi,YAŞA ATMACA Göknur,ERDOGMUS ALI,DEGE Mustafa Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. , 2018, ss.1375 - 1386. 10.18596/jotcsa.478665
AMA Şen P,YILDIZ S,Dege N,YAŞA ATMACA G,ERDOGMUS A,DEGE M Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. . 2018; 1375 - 1386. 10.18596/jotcsa.478665
Vancouver Şen P,YILDIZ S,Dege N,YAŞA ATMACA G,ERDOGMUS A,DEGE M Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. . 2018; 1375 - 1386. 10.18596/jotcsa.478665
IEEE Şen P,YILDIZ S,Dege N,YAŞA ATMACA G,ERDOGMUS A,DEGE M "Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study." , ss.1375 - 1386, 2018. 10.18596/jotcsa.478665
ISNAD Şen, Pınar vd. "Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study". (2018), 1375-1386. https://doi.org/10.18596/jotcsa.478665
APA Şen P, YILDIZ S, Dege N, YAŞA ATMACA G, ERDOGMUS A, DEGE M (2018). Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. Journal of the Turkish Chemical Society, Section A: Chemistry, 5(3), 1375 - 1386. 10.18596/jotcsa.478665
Chicago Şen Pınar,YILDIZ Salih Zeki,Dege Necmi,YAŞA ATMACA Göknur,ERDOGMUS ALI,DEGE Mustafa Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. Journal of the Turkish Chemical Society, Section A: Chemistry 5, no.3 (2018): 1375 - 1386. 10.18596/jotcsa.478665
MLA Şen Pınar,YILDIZ Salih Zeki,Dege Necmi,YAŞA ATMACA Göknur,ERDOGMUS ALI,DEGE Mustafa Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. Journal of the Turkish Chemical Society, Section A: Chemistry, vol.5, no.3, 2018, ss.1375 - 1386. 10.18596/jotcsa.478665
AMA Şen P,YILDIZ S,Dege N,YAŞA ATMACA G,ERDOGMUS A,DEGE M Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. Journal of the Turkish Chemical Society, Section A: Chemistry. 2018; 5(3): 1375 - 1386. 10.18596/jotcsa.478665
Vancouver Şen P,YILDIZ S,Dege N,YAŞA ATMACA G,ERDOGMUS A,DEGE M Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study. Journal of the Turkish Chemical Society, Section A: Chemistry. 2018; 5(3): 1375 - 1386. 10.18596/jotcsa.478665
IEEE Şen P,YILDIZ S,Dege N,YAŞA ATMACA G,ERDOGMUS A,DEGE M "Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study." Journal of the Turkish Chemical Society, Section A: Chemistry, 5, ss.1375 - 1386, 2018. 10.18596/jotcsa.478665
ISNAD Şen, Pınar vd. "Synthesis of a Novel Benzimidazole Moiety-Appended Schiff Base Derivative: Fluorescence and Chemosensor Study". Journal of the Turkish Chemical Society, Section A: Chemistry 5/3 (2018), 1375-1386. https://doi.org/10.18596/jotcsa.478665