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The new tetra substituted metallophthalocyanines bearing four Schiff bases on periphery: Synthesis, spectroscopic properties and investigation of the effect of various central metals on aggregation properties

Yıl 2020, Cilt: 2 Sayı: 1, 29 - 36, 23.06.2020

Halise Yalazan Ayşe Aktaş Kamiloğlu Halit Kantekin Ümmühan Ocak

Öz

In the present study, new Schiff base compound (Z)-4-((quinolin-2-ylmethyleneamino)methyl)phenol (3), its phthalonitrile derivative (Z)-4-(4-((quinolin-2-ylmethyleneamino)methyl)phenoxy)phthalonitrile (4) were synthesized in the first step. Then, zinc(II) (Pc‒5), cobalt(II) (Pc‒6) and copper(II) (Pc‒7) phthalocyanines containing Schiff base group with quinolin moiety on peripheral positions were synthesized. All new compounds were characterized by general spectroscopic techniques. Aggregation properties of the obtained metallophthalocyanines were researched in polar and apolar solvents.

Anahtar Kelimeler

Aggregation Metallophthalocyanine Phthalocyanine Schiff base

Destekleyen Kurum

Karadeniz Technical University

Teşekkür

This study was supported by the Research Fund of Karadeniz Technical University

Kaynakça

  • [1] C.C. Leznoff, A.B.P. Lever. 1989. Phthalocyanines: Properties and Applications, VCH Publishers, New York, , vol. 1.
  • [2] K. Kadish, K.M. Smith, R. (Eds.) Guilard, The Porphyrin Handbook, Academic Press, Boston, 2003, vol. 15–20.
  • [3] N.B. McKeown, Phthalocyanine Materials Synthesis, Structure and Function, Cambridge University Press, 1998.
  • [4] B. Ertem, H. Yalazan, Ö. Güngör, G. Sarkı, M. Durmuş, E.T. Saka, H. Kantekin, J. Luminescence, 204, 2018, 464‒471.
  • [5] H. Kantekin, E.T. Saka, B. Ertem, M.N. Mısır, H. Yalazan, G. Sarkı, J. Coord. Chem., 71:1, 2018, 164‒182.
  • [6] K. Kameyama, M. Morisue, A. Satake, Y. Kobuke, Angewandte Chemie International Edition, 44, 2005, 4763–4766.
  • [7] J.L. Sesler, J. Jayawickramarajah, A. Gouloumis, G.D. Patnos, T. Torres, D.M. Guldi, Tetrahedron, 62, 2006, 2123–2131.
  • [8] X. Huang, F.Q. Zhao, Z.Y. Li, L. Huang, Y.W. Tang, F. Zhang, C.H. Tung, Chemistry Letters, 36, 2007, 108–115.
  • [9] X. Huang, F.Q. Zhao, Z.Y. Li, Y.W. Tang, F. Zhang, C.H. Tung, Langmuir, 23, 2007, 5167–5172.
  • [10] M. Morisue, Y. Kobuke, Chemistry – A European Journal, 14, 2008, 4993–5000.
  • [11] H. Manfred, Alkaloids: Nature's Curse or Blessing?,Weinheim, Wiley-VCH, 2002.
  • [12] C.Y. Poon, P. Chiu, A synthesis of the tetracyclic carboskeleton of isaindigotidione. Tetrahedron Lett., 45, 2004, 2985-8.
  • [13] S. Ökten, O. Çakmak, Ş. Tekin, The structure activity relationship (SAR) study of 6,8-disubstituted quinoline derivatives as anti cancer agents, Turk J Clin Lab., 8(4), 2017, 152‒159.
  • [14] I. Jacquemond-Collet, F. Benoit-Vical, A. Valentin, E. Stanislas, M. Mallié, I. Fourasté Antiplasmodial and cytotoxic activity of galipinine and other tetrahydroquinolines from Galipea officinalis, Planta Med., 68(1), 2002, 68‒69.
  • [15] KC. Fang, YL. Chen, J. Sheu, T.C. Wang, C.C. Tzeng, Synthesis, antibacterial, and cytotoxic evaluation of certain 7-substituted norfloxacin derivatives, J Med Chem., 43, 20, 2000, 3809‒3812.
  • [16] P. Palit, P. Paira, A. Hazra, S. Banerjee, A.D. Gupta, S.G. Dastidar, N.B. Mondal, Phase transfer catalyzed synthesis of bisquinolines: Antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial evaluation, Eur J Med Chem., 44, 2009, 845−853.
  • [17] B. Podeszwa, H. Niedbala, J. Polanski, R. Musiol, D.Tabak, J.Finster, K. Serafin, M. Milczarek, J. Wietrzyk, S. Boryczka, W. Mol, J. Jampilek, J. Dohnal, D.S. Kalinowski, Dolezal, D.R. Richardson, Investigating the antiproliferative activity of quinoline-5,8-diones and styrylquinolinecarboxylic acids on tumor cell lines, Bioorganic & Medicinal Chemistry Letters, 17, 2007, 6138‒6141.
  • [18] R. Musiol, J. Jampilek, V. Buchta, et al. Antifungal properties of new series of quinoline derivatives, Bioorg Med Chem., 14, 2006, 3592‒3598.
  • [19] S. Ökten, O. Çakmak, R. Erenler, Ö.Y. Şahin, Ş. Tekin, Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities, Turk J Chem. 37, 2013, 896‒908.
  • [20] S. Ökten, Ö.Y. Şahin, Ş. Tekin, O. Çakmak, In vitro antiproliferative/ cytotoxic activity of novel quinoline compound SO-18 against various cancer cell lines, J Biotechn., 185S, 2014, S37‒125.
  • [21] F. Zouhiri, M. Danet, C. Benard, et al. HIV-1 replication inhibitors of the styrylquinoline class: Introduction of an additional carboxyl group at the C-5 position of the quinoline, Tetrahedron Lett., 46, 2005, 2201−2205.
  • [22] A. Şahin, O. Çakmak, İ. Demirtaş, S. Ökten, A. Tutar, Efficent and selective synthesis of quinoline derivatives, Tetrahedron, 64, 2008, 10068‒10074.
  • [23] S. Broch, B. Aboab, F. Anizon, P. Moreau, Synthesis and in vitro antiproliferative activities of quinoline derivatives, Eur J Med Chem., 45, 2010, 1657‒1662.
  • [24] J.E. Nycz, M. Szala, G.J. Malecki, M. Nowak, J. Kusz, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 117, 2014, 351‒359.
  • [25] B. Machura, J. Milek, J. Kusz, J. Nycz, D. Tabak, Polyhedron, 27, 2008, 1121‒1130.
  • [26] S.D. Lytton, B. Mester, I. Dayan, H. Glickstein, J. Libman, A. Shanzer, Z.I. Cabantchik, Blood, 81, 1993, 214–221.
  • [27] Z. Rezvani, L.R. Ahar, K. Nejati, S.M. Seyedahmadian, Acta Chim. Slov., 51, 2004, 675‒686.
  • [28] P. Sen, S.Z. Yildiz, M. Tuna, M. Canlica, J. Organomet. Chem., 769, 2014, 38‒45.
  • [29] S. Altun, A.R. Özkaya, M. Bulut, Polyhedron, 48, 2012, 31‒42.
  • [30] A.W. Snow, Phthalocyanine aggregation, in: K. Kadish, R. Guilard, K.M. Smith, The Porphyrin Handbook, Phthalocyanines: Properties and Materials, vol. 17, Academic Press, Amsterdam, 2003, pp. 129‒176.
  • [31] H. Enkelkamp, R.J.M. Nolte, J. Porphy. Phthalocyan., 4, 2000, 454‒459.
  • [32] D.D. Dominguez, A.W. Snow, J.S. Shirk, R.S. Pong, J. Porphy. Phthalocyan., 5, 2001, 582‒592.

Yıl 2020, Cilt: 2 Sayı: 1, 29 - 36, 23.06.2020

Halise Yalazan Ayşe Aktaş Kamiloğlu Halit Kantekin Ümmühan Ocak

Öz

Kaynakça

  • [1] C.C. Leznoff, A.B.P. Lever. 1989. Phthalocyanines: Properties and Applications, VCH Publishers, New York, , vol. 1.
  • [2] K. Kadish, K.M. Smith, R. (Eds.) Guilard, The Porphyrin Handbook, Academic Press, Boston, 2003, vol. 15–20.
  • [3] N.B. McKeown, Phthalocyanine Materials Synthesis, Structure and Function, Cambridge University Press, 1998.
  • [4] B. Ertem, H. Yalazan, Ö. Güngör, G. Sarkı, M. Durmuş, E.T. Saka, H. Kantekin, J. Luminescence, 204, 2018, 464‒471.
  • [5] H. Kantekin, E.T. Saka, B. Ertem, M.N. Mısır, H. Yalazan, G. Sarkı, J. Coord. Chem., 71:1, 2018, 164‒182.
  • [6] K. Kameyama, M. Morisue, A. Satake, Y. Kobuke, Angewandte Chemie International Edition, 44, 2005, 4763–4766.
  • [7] J.L. Sesler, J. Jayawickramarajah, A. Gouloumis, G.D. Patnos, T. Torres, D.M. Guldi, Tetrahedron, 62, 2006, 2123–2131.
  • [8] X. Huang, F.Q. Zhao, Z.Y. Li, L. Huang, Y.W. Tang, F. Zhang, C.H. Tung, Chemistry Letters, 36, 2007, 108–115.
  • [9] X. Huang, F.Q. Zhao, Z.Y. Li, Y.W. Tang, F. Zhang, C.H. Tung, Langmuir, 23, 2007, 5167–5172.
  • [10] M. Morisue, Y. Kobuke, Chemistry – A European Journal, 14, 2008, 4993–5000.
  • [11] H. Manfred, Alkaloids: Nature's Curse or Blessing?,Weinheim, Wiley-VCH, 2002.
  • [12] C.Y. Poon, P. Chiu, A synthesis of the tetracyclic carboskeleton of isaindigotidione. Tetrahedron Lett., 45, 2004, 2985-8.
  • [13] S. Ökten, O. Çakmak, Ş. Tekin, The structure activity relationship (SAR) study of 6,8-disubstituted quinoline derivatives as anti cancer agents, Turk J Clin Lab., 8(4), 2017, 152‒159.
  • [14] I. Jacquemond-Collet, F. Benoit-Vical, A. Valentin, E. Stanislas, M. Mallié, I. Fourasté Antiplasmodial and cytotoxic activity of galipinine and other tetrahydroquinolines from Galipea officinalis, Planta Med., 68(1), 2002, 68‒69.
  • [15] KC. Fang, YL. Chen, J. Sheu, T.C. Wang, C.C. Tzeng, Synthesis, antibacterial, and cytotoxic evaluation of certain 7-substituted norfloxacin derivatives, J Med Chem., 43, 20, 2000, 3809‒3812.
  • [16] P. Palit, P. Paira, A. Hazra, S. Banerjee, A.D. Gupta, S.G. Dastidar, N.B. Mondal, Phase transfer catalyzed synthesis of bisquinolines: Antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial evaluation, Eur J Med Chem., 44, 2009, 845−853.
  • [17] B. Podeszwa, H. Niedbala, J. Polanski, R. Musiol, D.Tabak, J.Finster, K. Serafin, M. Milczarek, J. Wietrzyk, S. Boryczka, W. Mol, J. Jampilek, J. Dohnal, D.S. Kalinowski, Dolezal, D.R. Richardson, Investigating the antiproliferative activity of quinoline-5,8-diones and styrylquinolinecarboxylic acids on tumor cell lines, Bioorganic & Medicinal Chemistry Letters, 17, 2007, 6138‒6141.
  • [18] R. Musiol, J. Jampilek, V. Buchta, et al. Antifungal properties of new series of quinoline derivatives, Bioorg Med Chem., 14, 2006, 3592‒3598.
  • [19] S. Ökten, O. Çakmak, R. Erenler, Ö.Y. Şahin, Ş. Tekin, Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities, Turk J Chem. 37, 2013, 896‒908.
  • [20] S. Ökten, Ö.Y. Şahin, Ş. Tekin, O. Çakmak, In vitro antiproliferative/ cytotoxic activity of novel quinoline compound SO-18 against various cancer cell lines, J Biotechn., 185S, 2014, S37‒125.
  • [21] F. Zouhiri, M. Danet, C. Benard, et al. HIV-1 replication inhibitors of the styrylquinoline class: Introduction of an additional carboxyl group at the C-5 position of the quinoline, Tetrahedron Lett., 46, 2005, 2201−2205.
  • [22] A. Şahin, O. Çakmak, İ. Demirtaş, S. Ökten, A. Tutar, Efficent and selective synthesis of quinoline derivatives, Tetrahedron, 64, 2008, 10068‒10074.
  • [23] S. Broch, B. Aboab, F. Anizon, P. Moreau, Synthesis and in vitro antiproliferative activities of quinoline derivatives, Eur J Med Chem., 45, 2010, 1657‒1662.
  • [24] J.E. Nycz, M. Szala, G.J. Malecki, M. Nowak, J. Kusz, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 117, 2014, 351‒359.
  • [25] B. Machura, J. Milek, J. Kusz, J. Nycz, D. Tabak, Polyhedron, 27, 2008, 1121‒1130.
  • [26] S.D. Lytton, B. Mester, I. Dayan, H. Glickstein, J. Libman, A. Shanzer, Z.I. Cabantchik, Blood, 81, 1993, 214–221.
  • [27] Z. Rezvani, L.R. Ahar, K. Nejati, S.M. Seyedahmadian, Acta Chim. Slov., 51, 2004, 675‒686.
  • [28] P. Sen, S.Z. Yildiz, M. Tuna, M. Canlica, J. Organomet. Chem., 769, 2014, 38‒45.
  • [29] S. Altun, A.R. Özkaya, M. Bulut, Polyhedron, 48, 2012, 31‒42.
  • [30] A.W. Snow, Phthalocyanine aggregation, in: K. Kadish, R. Guilard, K.M. Smith, The Porphyrin Handbook, Phthalocyanines: Properties and Materials, vol. 17, Academic Press, Amsterdam, 2003, pp. 129‒176.
  • [31] H. Enkelkamp, R.J.M. Nolte, J. Porphy. Phthalocyan., 4, 2000, 454‒459.
  • [32] D.D. Dominguez, A.W. Snow, J.S. Shirk, R.S. Pong, J. Porphy. Phthalocyan., 5, 2001, 582‒592.
Toplam 32 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Analitik Kimya
Bölüm Research Articles
Yazarlar

Halise Yalazan 0000-0003-1234-2721

Ayşe Aktaş Kamiloğlu 0000-0002-7347-4018

Halit Kantekin 0000-0003-2625-2815

Ümmühan Ocak 0000-0003-3696-4736

Yayımlanma Tarihi 23 Haziran 2020
Gönderilme Tarihi 21 Mayıs 2020
Kabul Tarihi 11 Haziran 2020
Yayımlandığı Sayı Yıl 2020 Cilt: 2 Sayı: 1

Kaynak Göster

APA Yalazan, H., Aktaş Kamiloğlu, A., Kantekin, H., Ocak, Ü. (2020). The new tetra substituted metallophthalocyanines bearing four Schiff bases on periphery: Synthesis, spectroscopic properties and investigation of the effect of various central metals on aggregation properties. Turkish Journal of Analytical Chemistry, 2(1), 29-36.
AMA Yalazan H, Aktaş Kamiloğlu A, Kantekin H, Ocak Ü. The new tetra substituted metallophthalocyanines bearing four Schiff bases on periphery: Synthesis, spectroscopic properties and investigation of the effect of various central metals on aggregation properties. TurkJAC. Haziran 2020;2(1):29-36.
Chicago Yalazan, Halise, Ayşe Aktaş Kamiloğlu, Halit Kantekin, ve Ümmühan Ocak. “The New Tetra Substituted Metallophthalocyanines Bearing Four Schiff Bases on Periphery: Synthesis, Spectroscopic Properties and Investigation of the Effect of Various Central Metals on Aggregation Properties”. Turkish Journal of Analytical Chemistry 2, sy. 1 (Haziran 2020): 29-36.
EndNote Yalazan H, Aktaş Kamiloğlu A, Kantekin H, Ocak Ü (01 Haziran 2020) The new tetra substituted metallophthalocyanines bearing four Schiff bases on periphery: Synthesis, spectroscopic properties and investigation of the effect of various central metals on aggregation properties. Turkish Journal of Analytical Chemistry 2 1 29–36.
IEEE H. Yalazan, A. Aktaş Kamiloğlu, H. Kantekin, ve Ü. Ocak, “The new tetra substituted metallophthalocyanines bearing four Schiff bases on periphery: Synthesis, spectroscopic properties and investigation of the effect of various central metals on aggregation properties”, TurkJAC, c. 2, sy. 1, ss. 29–36, 2020.
ISNAD Yalazan, Halise vd. “The New Tetra Substituted Metallophthalocyanines Bearing Four Schiff Bases on Periphery: Synthesis, Spectroscopic Properties and Investigation of the Effect of Various Central Metals on Aggregation Properties”. Turkish Journal of Analytical Chemistry 2/1 (Haziran 2020), 29-36.
JAMA Yalazan H, Aktaş Kamiloğlu A, Kantekin H, Ocak Ü. The new tetra substituted metallophthalocyanines bearing four Schiff bases on periphery: Synthesis, spectroscopic properties and investigation of the effect of various central metals on aggregation properties. TurkJAC. 2020;2:29–36.
MLA Yalazan, Halise vd. “The New Tetra Substituted Metallophthalocyanines Bearing Four Schiff Bases on Periphery: Synthesis, Spectroscopic Properties and Investigation of the Effect of Various Central Metals on Aggregation Properties”. Turkish Journal of Analytical Chemistry, c. 2, sy. 1, 2020, ss. 29-36.
Vancouver Yalazan H, Aktaş Kamiloğlu A, Kantekin H, Ocak Ü. The new tetra substituted metallophthalocyanines bearing four Schiff bases on periphery: Synthesis, spectroscopic properties and investigation of the effect of various central metals on aggregation properties. TurkJAC. 2020;2(1):29-36.
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