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Synthesis, Characterization and Structural Investigations of Two New Cu(II)-Pyridine-3,4-dicarboxylate Complexes

Yıl 2016, Cilt: 16 Sayı: 3, 531 - 543, 31.12.2016

Öz

In this study, new two Cu(II)-pyridine-3,4-dicarboxylate (3,4-pydc) complexes with 1,2-diaminoethane (en) and 1,3-diaminopropane (pen), Cu(3,4-pydc)(en)2 ]∙2H2O (1) and {[Cu(3,4-pydc)(pen)2 ][Cu(µ-3,4-pydc)(pen)2]∙H2O}n (2) have been synthesized and characterized by elemental analysis, FT-IR spectroscopy, UV–Vis. spectroscopy, thermal analysis and single crystal X-ray diffraction studies. The molecular structures of mononuclear 1 and both mono and polynuclear 2 complexes have been determined by the single crystal X-ray diffraction. In complex 1, Cu(II) ion was coordinated by 3,4-pydc ligand with its nitrogen atom in a monodentate manner. In complex 2, both Cu(II) ion was coordinated by 3,4-pydc ligand with its nitrogen atom in a monodentate manner and Cu(II) ion was coordinated by 3,4-pydc ligand with its nitrogen and oxygen atoms in a bidentate manner which exhibit bridged ligand. 3D supramolecular structures of complexes consist of N–H∙∙∙O and O–H∙∙∙O type hydrogen bonding interactions.

Kaynakça

  • Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. and Verschoor, G. C., 1984. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2[prime or minute]-yl)-2,6-dithiaheptane]copper(II) perchlorate, [10.1039/DT9840001349], Journal of the Chemical Society, Dalton Transactions, 7, 1349-1356.
  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. and Spagna, R., 1999. SIR97: a new tool for crystal structure determination and refinement,Journal of Applied Crystallography, 32, 115-119.
  • Chen, W., Yue, Q., Chen, C., Yuan, H. M., Xu, W., Chen, J. S. and Wang, S. N., 2003. Assembly of a manganese(II) pyridine-3,4-dicarboxylate polymeric network based on infinite Mn-O-C chains, 1, Dalton Transactions 1, 28-30.
  • Colak, A. T., Pamuk, G., Uzun, N., Yesilel, O. Z., Semerci, F., Gunay, H. and Buyukgungor, O., 2013. A Photoluminescent Polymeric 2D Silver(I) Complex Exhibits a Fishbone-like 1D Silver Cluster and New Coordination Mode of the Pyridine-2,3-Dicarboxylate, Journal of Inorganic and Organometallic Polymers and Materials, 23 (2), 418-423.
  • Crawford, S. M., 1963. The ultra-violet and visible spectra of some transition metal chelates with N, N'-bis-(o-hydroxybenzylidene) ethylenediamine and N, N'-bis-(o-hydroxybenzylidene)-o-phenylenediamine and related compounds, Spectrochimica Acta, 19 (1), 255-270.
  • Deacon, G. B. and Phillips, R. J., 1980. Relationships between the Carbon-Oxygen Stretching Frequencies of Carboxylato Complexes and the Type of Carboxylate Coordination, Coordination Chemistry Reviews, 33 (3), 227-250.
  • Eubank, J. F., Walsh, R. D., Poddar, P., Srikanth, H., Larsen, R. W. and Eddaoudi, M., 2006. Metal-organic framework diversity via heterocoordination of a multifunctional ligand: SrAl2 and a novel(3,4)-connected network, Crystal Growth & Design, 6 (6), 1453-1457.
  • Fu, Z. Y., Hu, S. M., Dai, J. C., Zhang, J. J. and Wu, X. T., 2003. Three novel polymeric frameworks assembled from Cd(II), Co(II), and Mn(II) with the mixed organic ligands 3,4-pyridinedicarboxylate, 1,3-bis(4-pyridyl)propane, or 1,2-bis(4-pyridyl)ethane, European Journal of Inorganic Chemistry, 14, 2670-2677.
  • Janiak, C., 2000. A critical account on pi-pi stacking in metal complexes with aromatic nitrogen-containing ligands, Journal of the Chemical Society-Dalton Transactions, 21, 3885-3896.
  • Janiak, C., 2003. Engineering coordination polymers towards applications, Dalton Transactions, 14, 2781-2804.
  • Kondo, M., Okubo, T., Asami, A., Noro, S., Yoshitomi, T., Kitagawa, S., Ishii, T., Matsuzaka, H. and Seki, K., 1999. Rational synthesis of stable channel-like cavities with methane gas adsorption properties: [{Cu-2(pzdc)(2)(L)}(n)] (pzdc = pyrazine-2,3-dicarboxylate; L = a pillar ligand), Angewandte Chemie-International Edition, 38 (1-2), 140-143.
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. and van De Streek, J., 2006. Mercury: visualization and analysis of crystal structures, Journal of Applied Crystallography, 39, 453-457.
  • Nakamoto, K., 1997. Applications in coordination chemistry, Infrared and Raman Spectra of Inorganic and Coordination Compounds: Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry, Sixth Edition 1-273.
  • Semerci, F., Yesilel, O. Z., Keskin, S., Darcan, C., Tas, M. and Dal, H., 2013. Construction of homo- and heterometallic-pyridine-2,3-dicarboxylate metallosupramolecular networks with structural diversity: 1D T5(2) water tape and unexpected coordination mode of pyridine-2,3-dicarboxylate, Crystengcomm, 15 (6), 1244-1256.
  • Semerci, F., Yesilel, O. Z., Olmez, H. and Buyukgungor, O., 2014. Supramolecular assemblies of copper(II)-pyridine-2,3-dicarboxylate complexes with N-donor ligands and clustered water molecules, Inorganica Chimica Acta, 409, 407-417.
  • Semerci, F., Yesilel, O. Z. and Sahin, E., 2010. Cu(II) and Zn(II)-Pyridine-2,3-Dicarboxylate Complexes with 2-Methylimidazole: Syntheses, Crystal Structures, Spectroscopic and Thermal Analyses, Journal of Inorganic and Organometallic Polymers and Materials, 20 (2), 334-342.
  • Semerci, F., Yesilel, O. Z., Sahin, E., Yerli, Y. and Topkaya, R., 2011. From Metalloligand to Extended 3D Network: Synthesis, Crystal Structure and Magnetic Property of {[Cu(en)(2)][Cu(mu(3)-pydc)(2)]center dot 6H(2)O} (n), Journal of Inorganic and Organometallic Polymers and Materials, 21 (2), 261-268.
  • Semerci, F., Yesilel, O. Z., Soylu, M. S., Keskin, S. and Buyukgungor, O., 2013. A two-dimensional photoluminescent cadmium(II)coordination polymer containing a new coordination mode of pyridine-2,3-dicarboxylate: Synthesis, structure and molecular simulations for gas storage and separation applications, Polyhedron, 50 (1), 314-320.
  • Semerci, F., Yesilel, O. Z., Soylu, M. S., Yerli, Y. and Dal, H., 2014. Two new pyridine-2,3-dicarboxylate coordination polymers prepared from zerovalent metal precursor: Syntheses, luminescent and magnetic properties, Journal of Solid State Chemistry, 210 (1), 224-231.
  • Semerci, F., Yesilel, O. Z. and Yuksel, F., 2015. Self-assembly of three new metal organic coordination networks based on 1,2-bis(imidazol-1yl-methyl)benzene, Polyhedron, 102, 1-7.
  • Semerci, F., Yesilel, O. Z., Yuksel, F. and Sahin, O., 2015. One-pot synthesis of two new metal-organic networks: hydrogen bonded mononuclear Cu(II) complex and mixed-valence Cu(I,II) coordination polymer with encapsulated 14-membered unique water cluster, Inorganic Chemistry Communications, 62, 29-33.
  • Semerci, F., Yeşilel, O. Z., Yüksel, F. and Şahin, O., 2016. Synthesis and characterization of new coordination polymers based on 2,3-/3,4-pyridinedicarboxylates and bispyridine ligands with structural diversity, Polyhedron, 111, 1-10.
  • Semerci, F., Yeþilel, O. and Þahin, E., 2010. Cu (II) and Zn (II)-Pyridine-2, 3-Dicarboxylate Complexes with 2-Methylimidazole: Syntheses, Crystal Structures, Spectroscopic and Thermal Analyses, Journal of Inorganic and Organometallic Polymers and Materials, 20 (2), 334-342.
  • Sheldrick, G. M. and Schneider, T. R., 1997. SHELXL: High-resolution refinement, Macromolecular Crystallography, Pt B, 277 (319-343.
  • Szorcsik, A., Nagy, L., Sletten, J., Szalontai, G., Kamu, E., Fiore, T., Pellerito, L. and Kalman, E., 2004. Preparation and structural studies on dibutyltin(IV) complexes with pyridine mono- and dicarboxylic acids, Journal of Organometallic Chemistry, 689 (7), 1145-1154.
  • Tong, M. L., Kitagawa, S., Chang, H. C. and Ohba, M., 2004. Temperature-controlled hydrothermal synthesis of a 2D ferromagnetic coordination bilayered polymer and a novel 3D network with inorganic CO3(OH)(2) ferrimagnetic chains, Chemical Communications 4), 418-419.
  • Yan, S. H., Li, X. X. and Zheng, X. J., 2009. Effect of the carboxyl groups on the assembly of copper pyridinedicarboxylate complexes, Journal of Molecular Structure, 929 (1-3), 105-111.
  • Yan, S. H., Zheng, X. J., Li, L. C., Yuan, D. Q. and Jin, L. P., 2011. Self-assembly and characterization of copper 3,4-pyridinedicarboxylate complexes based on a variety of polynuclear hydroxo clusters, Dalton Transactions, 40 (8), 1758-1767.
  • Yesilel, O., Mutlu, A., Darcan, C. and Büyükgüngör, O., 2009. Syntheses, structural characterization and antimicrobial activities of novel cobalt-pyrazine-2, 3-dicarboxylate complexes with N-donor ligands, Journal of Molecular Structure, 964, 39-46
  • Zhang, Q.-Z., Lu, C.-Z. and Xia, C.-K., 2005. A polymeric Mn complex with mixed pyridine-3,4-dicarboxylate/4,4′-bipyridine ligands: [Mn2(C7H3NO4)2(C10H8N2)2]n ∙ 2nH2O, Inorganic Chemistry Communications, 8 (3), 304-306.
  • Zhou, Y.-F., Yuan, D.-Q., Wu, B.-L., Wang, R.-H. and Hong, M.-C., 2004. Design of metal-organic NLO materials: complexes derived from pyridine-3,4-dicarboxylate, New Journal of Chemistry, 28 (12), 1590-1594.

İki Yeni Cu(II)-Piridin-3,4-dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu ve Yapısal Özelliklerinin İncelenmesi

Yıl 2016, Cilt: 16 Sayı: 3, 531 - 543, 31.12.2016

Öz

Bu çalışmada piridin-3,4-dikarboksilik asit (3,4-pydcH2) ve diamin türevi 1,2-diaminoetan (en) ve 1,3-diaminopropan (pen) ligantları kullanılarak karışık ligantlı [Cu(3,4-pydc)(en)2]∙2H2O (1) kompleksi ve {[Cu(3,4-pydc)(pen)2][Cu(μ-3,4-pydc)(pen)2]∙H2O}n (2) koordinasyon polimeri sentezlendi ve yapıları, elementel analiz, FT-IR spektroskopisi, UV-Vis spektroskopisi, termal analiz (TG/DTA) ve X-ışınları tek kristal çalışmaları ile aydınlatıldı. X-ışını tek kristal analizi çalışmaları sentezlenen 1 kompleksinin mononükleer, 2 kompleksinin yapısında ise hem mononükleer hem de 1D polinükleer yapının bulunduğunu göstermektedir. 3,4-pydc ligantı 1 kompleksinde tek dişli ligant olarak davranarak azot atomundan Cu(II) iyonuna koordine olmuştur. 2 kompleksinde ise mononükleer birimde azot atomundan tek dişli olarak, polinükleer birimde ise hem azot hem de karboksilat oksijen atomundan Cu(II) iyonlarını arasında köprü ligant özelliği sergilemektedir. Komplekslerin 3D supramoleküler yapıları, N–H∙∙∙O ve O–H∙∙∙O tipi hidrojen bağları etkileşimleri sayesinde oluşmaktadır.

Kaynakça

  • Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. and Verschoor, G. C., 1984. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2[prime or minute]-yl)-2,6-dithiaheptane]copper(II) perchlorate, [10.1039/DT9840001349], Journal of the Chemical Society, Dalton Transactions, 7, 1349-1356.
  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. and Spagna, R., 1999. SIR97: a new tool for crystal structure determination and refinement,Journal of Applied Crystallography, 32, 115-119.
  • Chen, W., Yue, Q., Chen, C., Yuan, H. M., Xu, W., Chen, J. S. and Wang, S. N., 2003. Assembly of a manganese(II) pyridine-3,4-dicarboxylate polymeric network based on infinite Mn-O-C chains, 1, Dalton Transactions 1, 28-30.
  • Colak, A. T., Pamuk, G., Uzun, N., Yesilel, O. Z., Semerci, F., Gunay, H. and Buyukgungor, O., 2013. A Photoluminescent Polymeric 2D Silver(I) Complex Exhibits a Fishbone-like 1D Silver Cluster and New Coordination Mode of the Pyridine-2,3-Dicarboxylate, Journal of Inorganic and Organometallic Polymers and Materials, 23 (2), 418-423.
  • Crawford, S. M., 1963. The ultra-violet and visible spectra of some transition metal chelates with N, N'-bis-(o-hydroxybenzylidene) ethylenediamine and N, N'-bis-(o-hydroxybenzylidene)-o-phenylenediamine and related compounds, Spectrochimica Acta, 19 (1), 255-270.
  • Deacon, G. B. and Phillips, R. J., 1980. Relationships between the Carbon-Oxygen Stretching Frequencies of Carboxylato Complexes and the Type of Carboxylate Coordination, Coordination Chemistry Reviews, 33 (3), 227-250.
  • Eubank, J. F., Walsh, R. D., Poddar, P., Srikanth, H., Larsen, R. W. and Eddaoudi, M., 2006. Metal-organic framework diversity via heterocoordination of a multifunctional ligand: SrAl2 and a novel(3,4)-connected network, Crystal Growth & Design, 6 (6), 1453-1457.
  • Fu, Z. Y., Hu, S. M., Dai, J. C., Zhang, J. J. and Wu, X. T., 2003. Three novel polymeric frameworks assembled from Cd(II), Co(II), and Mn(II) with the mixed organic ligands 3,4-pyridinedicarboxylate, 1,3-bis(4-pyridyl)propane, or 1,2-bis(4-pyridyl)ethane, European Journal of Inorganic Chemistry, 14, 2670-2677.
  • Janiak, C., 2000. A critical account on pi-pi stacking in metal complexes with aromatic nitrogen-containing ligands, Journal of the Chemical Society-Dalton Transactions, 21, 3885-3896.
  • Janiak, C., 2003. Engineering coordination polymers towards applications, Dalton Transactions, 14, 2781-2804.
  • Kondo, M., Okubo, T., Asami, A., Noro, S., Yoshitomi, T., Kitagawa, S., Ishii, T., Matsuzaka, H. and Seki, K., 1999. Rational synthesis of stable channel-like cavities with methane gas adsorption properties: [{Cu-2(pzdc)(2)(L)}(n)] (pzdc = pyrazine-2,3-dicarboxylate; L = a pillar ligand), Angewandte Chemie-International Edition, 38 (1-2), 140-143.
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. and van De Streek, J., 2006. Mercury: visualization and analysis of crystal structures, Journal of Applied Crystallography, 39, 453-457.
  • Nakamoto, K., 1997. Applications in coordination chemistry, Infrared and Raman Spectra of Inorganic and Coordination Compounds: Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry, Sixth Edition 1-273.
  • Semerci, F., Yesilel, O. Z., Keskin, S., Darcan, C., Tas, M. and Dal, H., 2013. Construction of homo- and heterometallic-pyridine-2,3-dicarboxylate metallosupramolecular networks with structural diversity: 1D T5(2) water tape and unexpected coordination mode of pyridine-2,3-dicarboxylate, Crystengcomm, 15 (6), 1244-1256.
  • Semerci, F., Yesilel, O. Z., Olmez, H. and Buyukgungor, O., 2014. Supramolecular assemblies of copper(II)-pyridine-2,3-dicarboxylate complexes with N-donor ligands and clustered water molecules, Inorganica Chimica Acta, 409, 407-417.
  • Semerci, F., Yesilel, O. Z. and Sahin, E., 2010. Cu(II) and Zn(II)-Pyridine-2,3-Dicarboxylate Complexes with 2-Methylimidazole: Syntheses, Crystal Structures, Spectroscopic and Thermal Analyses, Journal of Inorganic and Organometallic Polymers and Materials, 20 (2), 334-342.
  • Semerci, F., Yesilel, O. Z., Sahin, E., Yerli, Y. and Topkaya, R., 2011. From Metalloligand to Extended 3D Network: Synthesis, Crystal Structure and Magnetic Property of {[Cu(en)(2)][Cu(mu(3)-pydc)(2)]center dot 6H(2)O} (n), Journal of Inorganic and Organometallic Polymers and Materials, 21 (2), 261-268.
  • Semerci, F., Yesilel, O. Z., Soylu, M. S., Keskin, S. and Buyukgungor, O., 2013. A two-dimensional photoluminescent cadmium(II)coordination polymer containing a new coordination mode of pyridine-2,3-dicarboxylate: Synthesis, structure and molecular simulations for gas storage and separation applications, Polyhedron, 50 (1), 314-320.
  • Semerci, F., Yesilel, O. Z., Soylu, M. S., Yerli, Y. and Dal, H., 2014. Two new pyridine-2,3-dicarboxylate coordination polymers prepared from zerovalent metal precursor: Syntheses, luminescent and magnetic properties, Journal of Solid State Chemistry, 210 (1), 224-231.
  • Semerci, F., Yesilel, O. Z. and Yuksel, F., 2015. Self-assembly of three new metal organic coordination networks based on 1,2-bis(imidazol-1yl-methyl)benzene, Polyhedron, 102, 1-7.
  • Semerci, F., Yesilel, O. Z., Yuksel, F. and Sahin, O., 2015. One-pot synthesis of two new metal-organic networks: hydrogen bonded mononuclear Cu(II) complex and mixed-valence Cu(I,II) coordination polymer with encapsulated 14-membered unique water cluster, Inorganic Chemistry Communications, 62, 29-33.
  • Semerci, F., Yeşilel, O. Z., Yüksel, F. and Şahin, O., 2016. Synthesis and characterization of new coordination polymers based on 2,3-/3,4-pyridinedicarboxylates and bispyridine ligands with structural diversity, Polyhedron, 111, 1-10.
  • Semerci, F., Yeþilel, O. and Þahin, E., 2010. Cu (II) and Zn (II)-Pyridine-2, 3-Dicarboxylate Complexes with 2-Methylimidazole: Syntheses, Crystal Structures, Spectroscopic and Thermal Analyses, Journal of Inorganic and Organometallic Polymers and Materials, 20 (2), 334-342.
  • Sheldrick, G. M. and Schneider, T. R., 1997. SHELXL: High-resolution refinement, Macromolecular Crystallography, Pt B, 277 (319-343.
  • Szorcsik, A., Nagy, L., Sletten, J., Szalontai, G., Kamu, E., Fiore, T., Pellerito, L. and Kalman, E., 2004. Preparation and structural studies on dibutyltin(IV) complexes with pyridine mono- and dicarboxylic acids, Journal of Organometallic Chemistry, 689 (7), 1145-1154.
  • Tong, M. L., Kitagawa, S., Chang, H. C. and Ohba, M., 2004. Temperature-controlled hydrothermal synthesis of a 2D ferromagnetic coordination bilayered polymer and a novel 3D network with inorganic CO3(OH)(2) ferrimagnetic chains, Chemical Communications 4), 418-419.
  • Yan, S. H., Li, X. X. and Zheng, X. J., 2009. Effect of the carboxyl groups on the assembly of copper pyridinedicarboxylate complexes, Journal of Molecular Structure, 929 (1-3), 105-111.
  • Yan, S. H., Zheng, X. J., Li, L. C., Yuan, D. Q. and Jin, L. P., 2011. Self-assembly and characterization of copper 3,4-pyridinedicarboxylate complexes based on a variety of polynuclear hydroxo clusters, Dalton Transactions, 40 (8), 1758-1767.
  • Yesilel, O., Mutlu, A., Darcan, C. and Büyükgüngör, O., 2009. Syntheses, structural characterization and antimicrobial activities of novel cobalt-pyrazine-2, 3-dicarboxylate complexes with N-donor ligands, Journal of Molecular Structure, 964, 39-46
  • Zhang, Q.-Z., Lu, C.-Z. and Xia, C.-K., 2005. A polymeric Mn complex with mixed pyridine-3,4-dicarboxylate/4,4′-bipyridine ligands: [Mn2(C7H3NO4)2(C10H8N2)2]n ∙ 2nH2O, Inorganic Chemistry Communications, 8 (3), 304-306.
  • Zhou, Y.-F., Yuan, D.-Q., Wu, B.-L., Wang, R.-H. and Hong, M.-C., 2004. Design of metal-organic NLO materials: complexes derived from pyridine-3,4-dicarboxylate, New Journal of Chemistry, 28 (12), 1590-1594.
Toplam 31 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Fatih Semerci

Yayımlanma Tarihi 31 Aralık 2016
Gönderilme Tarihi 27 Nisan 2016
Yayımlandığı Sayı Yıl 2016 Cilt: 16 Sayı: 3

Kaynak Göster

APA Semerci, F. (2016). İki Yeni Cu(II)-Piridin-3,4-dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu ve Yapısal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 16(3), 531-543.
AMA Semerci F. İki Yeni Cu(II)-Piridin-3,4-dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu ve Yapısal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. Aralık 2016;16(3):531-543.
Chicago Semerci, Fatih. “İki Yeni Cu(II)-Piridin-3,4-Dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu Ve Yapısal Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 16, sy. 3 (Aralık 2016): 531-43.
EndNote Semerci F (01 Aralık 2016) İki Yeni Cu(II)-Piridin-3,4-dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu ve Yapısal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 16 3 531–543.
IEEE F. Semerci, “İki Yeni Cu(II)-Piridin-3,4-dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu ve Yapısal Özelliklerinin İncelenmesi”, Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, c. 16, sy. 3, ss. 531–543, 2016.
ISNAD Semerci, Fatih. “İki Yeni Cu(II)-Piridin-3,4-Dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu Ve Yapısal Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 16/3 (Aralık 2016), 531-543.
JAMA Semerci F. İki Yeni Cu(II)-Piridin-3,4-dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu ve Yapısal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2016;16:531–543.
MLA Semerci, Fatih. “İki Yeni Cu(II)-Piridin-3,4-Dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu Ve Yapısal Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, c. 16, sy. 3, 2016, ss. 531-43.
Vancouver Semerci F. İki Yeni Cu(II)-Piridin-3,4-dikarboksilat Komplekslerinin Sentezi, Karakterizasyonu ve Yapısal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2016;16(3):531-43.