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İyodo Piridin Sübstitüe Çift Kollu Benzo-15-crown-5 Bileşiği ve Komplekslerinin Eldesi, Spektroskopik ve Termal Özelliklerinin İncelenmesi

Year 2022, , 359 - 370, 25.11.2022
https://doi.org/10.29233/sdufeffd.1115685

Abstract

Bu çalışmada 4′,5′-bis(bromometil)benzo-15-crown-5 ile 2-iyodo-3-hidroksipiridin etkileştirilerek, yeni, çift kollu taç eter ligandı (L) sentezlenmiştir. Sentezlenen ligand (L), Na+ ve K+ kompleksi elde etmek üzere sodyum pikrat ve potasyum pikrat ile tepkimeye sokulmuştur. Böylelikle, benzo-15-crown-5’in halka boşluğuna uygun olan Na+ ile 1:1 (filling) kompleksi (NaL) ve halka boşluğundan daha büyük olan K+ ile 1:2 (sandviç) kompleksi (KL2) elde edilmiştir. Ayrıca bileşik L’nin gümüş nitrat ile reaksiyonu sonucunda geçiş metal kompleksi (AgL) sentezlenmiştir. Elde edilen ligand ve komplekslerin yapısı, spektroskopik yöntemler (FTIR, HRMS, 1H-NMR, 13C-NMR) kullanılarak aydınlatılmıştır. Son olarak, sentezlenen ligand ve komplekslerin termal özellikleri TGA - DTA yöntemleri kullanılarak incelenmiş ve bileşik yapıları ile uyumlu sonuçlar elde edilmiştir.

Thanks

Bu çalışmaya verdiği desteklerden dolayı Prof. Dr. Zeliha HAYVALI’ya, FTIR ve termal analizlerdeki yardımlarından dolayı Erdal EMİR’e teşekkürlerimi sunarım.

References

  • ,C.J. Pedersen, “Cyclic polyethers and their complexes with metal salts”, J. Am. Chem. Soc., 89, 7017-7036, 1967.
  • C. J. Pedersen and H. K. Frensdorff, “Macrocyclic polyethers and their complexes”, Angew. Chem. Int. Edit., 11 (1), 16-26, 1972.
  • G. W. Gokel, “Crown Ethers” in Encyclopedia of Supramolecular Chemistry, 1st ed. vol. 1, J. L. Atwood, J. W. Steed ed.2004., Taylor&Francis Group, Northwest, USA 2004, pp. 326-333.
  • N. S. Poonia and A. V. Bajaj, “Coordination chemistry of alkali and alkaline earth cations”, Chem. Rev., 79 (5), 389-445, 1979.
  • A. Bencini, V. Lippolis, J. M. López-de-Luzuriaga and M. E. Olmos, “On the use of mixed thia/aza macrocycles in the development of fluorescent chemosensors for toxic heavy metals and fluorescent materials”, Phosphorus Sulfur., 194 (7), 682-688, 2019.
  • A. M. Hodorogea, A. Silvertru, V. Lippolis and A. Pop “Group 12 metal complexes of mixed thia/aza and thia/oxa/aza macrocyclic ligands”, Polyhedron, 216, 115650, 2022.
  • C. L. Liotta and H. P. Harris, “Chemistry of naked anions. I. Reactions of the 18-crown-6 complex of potassium fluoride with organic substrates in aprotic organic solvents”, J. Am. Chem. Soc., 96 (7), 2250-2252, 1974.
  • S. Kurella, J. K. Basu and S. Sengupta, “Study of solid-liquid phase transfer catalysed reaction to produce p-nitroanisole using 18-crown-6 as catalyst”, Indian Chem.Eng., 59 (1), 31-40, 2015.
  • F. Supek, T. Ramljak, M. Marjanović, M. Buljubašić, G. Kragol, N. Ilić, T. Šmuc, D. Zahradka, K. Mlinarić-Majerski and M. Kralj, “Could LogP be a principal determinant of biological activity in 18-crown-6 ethers? Synthesis of biologically active adamantane-substituted diaza-crowns”, Eur. J. Med. Chem., 46, 3444-3454, 2011.
  • Z. Hayvalı, H. Güler and H. Öğütçü, “Novel bis-crown ethers and their sodium complexes as antimicrobial agent: synthesis and spectroscopic characterizations”, Med. Chem. Res., 23, 3652-3661, 2014.
  • M. Barboiu, “Encapsulation versus self-aggregation toward highly selective artificial K+ channels”, Accounts. Chem. Res., 51, 2711-2718, 2018.
  • S. Shinkai, T. Minami, Y. Kusano and O. Manabe, “Photoresponsive crown ethers. 5. Light-driven ion transport by crown ethers with a photoresponsive anionic cap”, J. Am. Chem. Soc., 104, 1967-1972, 1982.
  • A. I. Vedernikov, E. N. Ushakov, L. G. Kuzmina, A. V. Churakov, Y. A. Strelenko, M. Wörner, A. M. Braun, J. A. K. Howard, M. V. Alfimov S. P. and Gromov, S.P. “New dithiacrown–ether butadienyl dyes: synthesis, structure, and complex formation with heavy metal cations”, J. Phys. Org. Chem., 23, 195-206, 2010.
  • L. Zhao, X. Chen, F. Guo, B. Gou, C. Yang and W. Xia, “Luminescent properties and logic nature of a crown Schiff base responding to sodium ion and zinc ion”, J. Lumin., 145, 486-491, 2014.
  • K: Sako, T. Kakehi, S. Nakano, H. Oku, X. F. Shen, T. Iwanaga, M. Yoshikawa, K. Sugahara, S. Toyota, H. Takemura, T. Shinmyozu, M: Shiotsuka and H. Tatemitsu, “Synthesis and properties of novel crown ether-annelated 4′, 5′-diaza-9′-(1, 3-dithiole-2-ylidene)-fluorenes and their ruthenium (II) complexes”, Tetrahedron Lett., 55, 749-752, 2014.
  • Q. Diao, P. Ma, L. Lv, T. Li, X. Wang and D. Song, “A novel fluorescent probe for Cr3+ based on rhodamine–crown ether conjugate and its application to drinking water examination and bioimaging”, Spectrochim. Acta A, 156, 15-21, 2016.
  • D. Şahin, H. Yılmaz and Z. Hayvalı, “Synthesis, spectroscopic and spectrophotometric study of BODIPY appended crown ether sensor for ion detection”, Res. Chem. Intermediat., 42, 6337-6350, 2016.
  • E. Luboch, A. Cygan and J. F. Biernat, “The synthesis of some aromatic crown ether derivatives and their ion-selective electrode properties” Tetrahedron, 46, 2461-2472, 1990.
  • M. J. Calverley and J. Dale, “l, 4, 7‑Trioxa‑10‑azacyclododecane and some N‑substituted derivatives; Synthesis and cation complexing”, Acta Chem. Scand. B., 36, 241-247, 1982.
  • M. C. Sanchez, P. C. Isolani, J. Zukerman-Schpector and G. Vicentini, “Characterization and structure of hydrated scandium (III) picrate: complexes with sulfoxide ligands”, J. Alloy. Compd., 344, 298-303, 2002.
  • D. C. Zhong, Z. F. Chen, Y. C. Liu, X. J. Luo, C. Barta and H. Liang, “Syntheses, crystal structures of Ni (II), Ag (I)-enoxacin complexes, and their antibacterial activity”, J. Coord. Chem., 63, 3146-3154, 2010.
  • V. V. Medviediev and M. Daszkiewicz, “Intermolecular interactions in 2-methyl-3-nitroanilinium nitrate, sulphate and dihydrogen phosphate in a view of topological approach and vibrational spectra”, J. Mol. Struct., 1229, 129577, 2021.
  • N. Ghildiyal, G. J. Nee Pant, M. S. M. Rawat and K. Singh, “Spectral investigation of the effect of anion on the stability of non covalent assemblies of 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine (benzo-15-crown-5) with sodium halides”, Spectrochim. Acta A, 171, 507-514, 2017.
  • Z. Hayvalı and P. Köksal, “Syntheses and spectroscopic characterization of double-armed benzo-15-crown-5 derivatives and their sodium and potassium complexes”, J. Inc. Phenom. Macro., 76, 369-378, 2013.
  • Y.Liu, J. R. Han and H. Y. Zhang, “Assembly behavior and binding ability of double-armed benzo-15-crown-5 with the potassium ion”, Supramol. Chem., 16, 247-254, 2004.
  • S. Kocoglu, Z. Hayvalı and H. Ogutcu, “A polydentate ligand based on 2,2’-dipyridylamine unit linked benzo-15-crown-5; alkali and transition metal complexes; photoresponsive ligand; antimicrobial evaluation against pathogenic microorganisms”, Transit. Metal Chem., 46 (7), 509-522, 2021.
  • M. Matsukawa, M. Matsunaga, M. Yoshida and S. Fujiwara, “Synthesis of transition metal picrates”, Sci. Technol Energ. Ma: J. Japan Explos. Soc., 65 (1), 1-6, 2004.
  • R. Liu, T. Zhang, L. Yang and Z. Zhou, “Effect of particle size on thermal decomposition of alkali metal picrates”, Thermochim. Acta, 583, 78-85, 2014.

Preparation of Double Armed Iodo Pyridine Substituted Benzo-15-crown-5 Ligand and Complexes, Investigation of Spectroscopic and Thermal Properties

Year 2022, , 359 - 370, 25.11.2022
https://doi.org/10.29233/sdufeffd.1115685

Abstract

In this study, a new double-armed crown ether ligand (L) was synthesized by interacting 4',5'-bis(bromomethyl)benzo-15-crown-5 and 2-iodo-3-hydroxypyridine. Synthesized ligand (L) was reacted with sodium picrate and potassium picrate to obtain a Na+ and K+ complex. In this way, a 1:1 (filling) complex (NaL) with Na+ conforming to the cavity size of benzo-15-crown-5 and a 1:2 (sandwich) complex (KL2) with K+ larger than the cavity size were obtained. In addition, transition metal complex (AgL) was synthesized from the reaction of compound L with silver nitrate. The structure of the obtained ligands and complexes were characterized using spectroscopic methods (FTIR, HRMS, 1H-NMR, 13C-NMR). Finally, the thermal properties of the synthesized ligand and complexes were investigated using TGA - DTA methods and the results were observed compatible with the structures of the compounds.

References

  • ,C.J. Pedersen, “Cyclic polyethers and their complexes with metal salts”, J. Am. Chem. Soc., 89, 7017-7036, 1967.
  • C. J. Pedersen and H. K. Frensdorff, “Macrocyclic polyethers and their complexes”, Angew. Chem. Int. Edit., 11 (1), 16-26, 1972.
  • G. W. Gokel, “Crown Ethers” in Encyclopedia of Supramolecular Chemistry, 1st ed. vol. 1, J. L. Atwood, J. W. Steed ed.2004., Taylor&Francis Group, Northwest, USA 2004, pp. 326-333.
  • N. S. Poonia and A. V. Bajaj, “Coordination chemistry of alkali and alkaline earth cations”, Chem. Rev., 79 (5), 389-445, 1979.
  • A. Bencini, V. Lippolis, J. M. López-de-Luzuriaga and M. E. Olmos, “On the use of mixed thia/aza macrocycles in the development of fluorescent chemosensors for toxic heavy metals and fluorescent materials”, Phosphorus Sulfur., 194 (7), 682-688, 2019.
  • A. M. Hodorogea, A. Silvertru, V. Lippolis and A. Pop “Group 12 metal complexes of mixed thia/aza and thia/oxa/aza macrocyclic ligands”, Polyhedron, 216, 115650, 2022.
  • C. L. Liotta and H. P. Harris, “Chemistry of naked anions. I. Reactions of the 18-crown-6 complex of potassium fluoride with organic substrates in aprotic organic solvents”, J. Am. Chem. Soc., 96 (7), 2250-2252, 1974.
  • S. Kurella, J. K. Basu and S. Sengupta, “Study of solid-liquid phase transfer catalysed reaction to produce p-nitroanisole using 18-crown-6 as catalyst”, Indian Chem.Eng., 59 (1), 31-40, 2015.
  • F. Supek, T. Ramljak, M. Marjanović, M. Buljubašić, G. Kragol, N. Ilić, T. Šmuc, D. Zahradka, K. Mlinarić-Majerski and M. Kralj, “Could LogP be a principal determinant of biological activity in 18-crown-6 ethers? Synthesis of biologically active adamantane-substituted diaza-crowns”, Eur. J. Med. Chem., 46, 3444-3454, 2011.
  • Z. Hayvalı, H. Güler and H. Öğütçü, “Novel bis-crown ethers and their sodium complexes as antimicrobial agent: synthesis and spectroscopic characterizations”, Med. Chem. Res., 23, 3652-3661, 2014.
  • M. Barboiu, “Encapsulation versus self-aggregation toward highly selective artificial K+ channels”, Accounts. Chem. Res., 51, 2711-2718, 2018.
  • S. Shinkai, T. Minami, Y. Kusano and O. Manabe, “Photoresponsive crown ethers. 5. Light-driven ion transport by crown ethers with a photoresponsive anionic cap”, J. Am. Chem. Soc., 104, 1967-1972, 1982.
  • A. I. Vedernikov, E. N. Ushakov, L. G. Kuzmina, A. V. Churakov, Y. A. Strelenko, M. Wörner, A. M. Braun, J. A. K. Howard, M. V. Alfimov S. P. and Gromov, S.P. “New dithiacrown–ether butadienyl dyes: synthesis, structure, and complex formation with heavy metal cations”, J. Phys. Org. Chem., 23, 195-206, 2010.
  • L. Zhao, X. Chen, F. Guo, B. Gou, C. Yang and W. Xia, “Luminescent properties and logic nature of a crown Schiff base responding to sodium ion and zinc ion”, J. Lumin., 145, 486-491, 2014.
  • K: Sako, T. Kakehi, S. Nakano, H. Oku, X. F. Shen, T. Iwanaga, M. Yoshikawa, K. Sugahara, S. Toyota, H. Takemura, T. Shinmyozu, M: Shiotsuka and H. Tatemitsu, “Synthesis and properties of novel crown ether-annelated 4′, 5′-diaza-9′-(1, 3-dithiole-2-ylidene)-fluorenes and their ruthenium (II) complexes”, Tetrahedron Lett., 55, 749-752, 2014.
  • Q. Diao, P. Ma, L. Lv, T. Li, X. Wang and D. Song, “A novel fluorescent probe for Cr3+ based on rhodamine–crown ether conjugate and its application to drinking water examination and bioimaging”, Spectrochim. Acta A, 156, 15-21, 2016.
  • D. Şahin, H. Yılmaz and Z. Hayvalı, “Synthesis, spectroscopic and spectrophotometric study of BODIPY appended crown ether sensor for ion detection”, Res. Chem. Intermediat., 42, 6337-6350, 2016.
  • E. Luboch, A. Cygan and J. F. Biernat, “The synthesis of some aromatic crown ether derivatives and their ion-selective electrode properties” Tetrahedron, 46, 2461-2472, 1990.
  • M. J. Calverley and J. Dale, “l, 4, 7‑Trioxa‑10‑azacyclododecane and some N‑substituted derivatives; Synthesis and cation complexing”, Acta Chem. Scand. B., 36, 241-247, 1982.
  • M. C. Sanchez, P. C. Isolani, J. Zukerman-Schpector and G. Vicentini, “Characterization and structure of hydrated scandium (III) picrate: complexes with sulfoxide ligands”, J. Alloy. Compd., 344, 298-303, 2002.
  • D. C. Zhong, Z. F. Chen, Y. C. Liu, X. J. Luo, C. Barta and H. Liang, “Syntheses, crystal structures of Ni (II), Ag (I)-enoxacin complexes, and their antibacterial activity”, J. Coord. Chem., 63, 3146-3154, 2010.
  • V. V. Medviediev and M. Daszkiewicz, “Intermolecular interactions in 2-methyl-3-nitroanilinium nitrate, sulphate and dihydrogen phosphate in a view of topological approach and vibrational spectra”, J. Mol. Struct., 1229, 129577, 2021.
  • N. Ghildiyal, G. J. Nee Pant, M. S. M. Rawat and K. Singh, “Spectral investigation of the effect of anion on the stability of non covalent assemblies of 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine (benzo-15-crown-5) with sodium halides”, Spectrochim. Acta A, 171, 507-514, 2017.
  • Z. Hayvalı and P. Köksal, “Syntheses and spectroscopic characterization of double-armed benzo-15-crown-5 derivatives and their sodium and potassium complexes”, J. Inc. Phenom. Macro., 76, 369-378, 2013.
  • Y.Liu, J. R. Han and H. Y. Zhang, “Assembly behavior and binding ability of double-armed benzo-15-crown-5 with the potassium ion”, Supramol. Chem., 16, 247-254, 2004.
  • S. Kocoglu, Z. Hayvalı and H. Ogutcu, “A polydentate ligand based on 2,2’-dipyridylamine unit linked benzo-15-crown-5; alkali and transition metal complexes; photoresponsive ligand; antimicrobial evaluation against pathogenic microorganisms”, Transit. Metal Chem., 46 (7), 509-522, 2021.
  • M. Matsukawa, M. Matsunaga, M. Yoshida and S. Fujiwara, “Synthesis of transition metal picrates”, Sci. Technol Energ. Ma: J. Japan Explos. Soc., 65 (1), 1-6, 2004.
  • R. Liu, T. Zhang, L. Yang and Z. Zhou, “Effect of particle size on thermal decomposition of alkali metal picrates”, Thermochim. Acta, 583, 78-85, 2014.
There are 28 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Makaleler
Authors

Serhat Koçoğlu 0000-0002-3590-9084

Publication Date November 25, 2022
Published in Issue Year 2022

Cite

IEEE S. Koçoğlu, “İyodo Piridin Sübstitüe Çift Kollu Benzo-15-crown-5 Bileşiği ve Komplekslerinin Eldesi, Spektroskopik ve Termal Özelliklerinin İncelenmesi”, Süleyman Demirel University Faculty of Arts and Science Journal of Science, vol. 17, no. 2, pp. 359–370, 2022, doi: 10.29233/sdufeffd.1115685.