A novel Benzimidazole moiety-appended Schiff base derivative: Synthesis, characterization and the investigation of photophysical and chemosensor properties

Pınar Şen; Salih Zeki Yıldız; Necmi Dege; Göknur Yaşa Atmaca; Ali Erdoğmuş; Mustafa Dege

doi:10.18596/jotcsa.478665

Araştırma Makalesi

A novel Benzimidazole moiety-appended Schiff base derivative: Synthesis, characterization and the investigation of photophysical and chemosensor properties

Yıl 2018, Cilt: 5 Sayı: 3, 1375 - 1386, 01.09.2018

Pınar Şen Salih Zeki Yıldız Necmi Dege Göknur Yaşa Atmaca Ali Erdoğmuş Mustafa Dege

https://doi.org/10.18596/jotcsa.478665

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 by the
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 was fully characterized by FT-IR, UV–vis, ¹H-NMR,
¹³C-NMR and mass spectroscopy. Electronic absorption and
fluorescence titration studies of 3
with different metal cations in a DMF show a highly selective binding affinity
only toward and Zn²⁺ ion. The crystal
structure of 2, C₈H₁₃Cl₂N₃O,
has been determined by single crystal X-ray
diffraction method. The crystal structure of the title compound, C₈H₁₁N₃²⁺×2(Cl^—)×H₂O, consists of an organic 1H-benzoimidazol-3-ium
(C₈H₁₁N₃²⁺) cation, an inorganic
2(Cl^—) anion and one water (H₂O) molecule. In the
cation of the title compound, C₈H₁₁N₃²⁺,
the benzimidazole ring system is planar with a maximum deviation of -0.012
(3) Å. The crystal
belongs to monoclinic system, space group P2₁/c. The crystal packing is stabilized by intramolecular
N–H···O, N–H···Cl, the intermolecular
N–H···Cl interactions link the molecules into a
two-dimensional network and between anions and the water molecules. π-π contacts between benzimidazole rings
[centroid–centroid distances = 3.4642 (2) Å,
3.5309 (2) Å and 3.5527 (2) Å] may further stabilize the structure.

Anahtar Kelimeler

Synthesis, benzimidazole derivative, Schiff base, Single crystal, X-ray crystallography, Crystal structure, Fluorescence property

Kaynakça

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 anti-inflammatory 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 Schiff-base 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 X-RED32 (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(1H-benzimidazolium)(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-1H-benzoimidazol-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.

Yıl 2018, Cilt: 5 Sayı: 3, 1375 - 1386, 01.09.2018

Pınar Şen Salih Zeki Yıldız Necmi Dege Göknur Yaşa Atmaca Ali Erdoğmuş Mustafa Dege

https://doi.org/10.18596/jotcsa.478665

Öz

Kaynakça

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 anti-inflammatory 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 Schiff-base 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 X-RED32 (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(1H-benzimidazolium)(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-1H-benzoimidazol-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.

Toplam 33 adet kaynakça vardır.

Ayrıntılar

Birincil Dil	İngilizce
Konular	Kimya Mühendisliği
Bölüm	Makaleler
Yazarlar	Pınar Şen 0000-0002-3181-9890 Salih Zeki Yıldız Necmi Dege 0000-0003-0660-4721 Göknur Yaşa Atmaca Bu kişi benim Ali Erdoğmuş Mustafa Dege Bu kişi benim
Yayımlanma Tarihi	1 Eylül 2018
Gönderilme Tarihi	5 Kasım 2018
Kabul Tarihi	25 Aralık 2018
Yayımlandığı Sayı	Yıl 2018 Cilt: 5 Sayı: 3

Kaynak Göster

Vancouver	Şen P, Yıldız SZ, Dege N, Atmaca GY, Erdoğmuş A, Dege M. A novel Benzimidazole moiety-appended Schiff base derivative: Synthesis, characterization and the investigation of photophysical and chemosensor properties. JOTCSA. 2018;5(3):1375-86.

Kapak Resmi İndir

Makale Dosyaları

Tam Metin

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.