Bazı Yeni Karbazol-Metal Komplekslerinin Sentezi ve Termal, Elektronik, Spektral ve Katalitik Alken Oksidasyon Özellikleri

Year 2020, , 189 - 206, 25.06.2020

Selma Bal

https://doi.org/10.37094/adyujsci.705453

Abstract

İki yeni ligant [(E)-4-kloro-2-((9-etil-9H-karbazol-3-yl)metilenamino)fenol, (E)-2-bromo4-chloro-6-((9-etil-9H-karbazol-3-yl)metilenamino)fenol] ile bunların kobalt (II), mangan (II) ve nikel(II) kompleksleri sentezlenmiş ve yapıları değişik spektroskopik yöntemlerle (NMR, UV, IR, Mass etc.) karakterize edilmişlerdir. Sentezlenen bileşiklerin katalitik aktiviteleri stiren ve siklohekzenin oksidasyon reaksiyonları üzerinde incelenmiştir. Her iki ligantın Mangan (II) kompleksleri alken oksidasyonlarında en yüksek aktiviteyi göstermiştir. Sentezlenen kompleks bileşiklerin katalizör olarak yüksek sıcaklık isteyen katalitik reaksiyonlarda kullanılabilirliği termal analizlerle kanıtlanmıştır. Bu yeni bileşiklerin elektronik özellikleri de ilk kez bu çalışma ile rapor edilmektedir. 

Keywords

Kataliz, Kompleks, Şifbazı

Supporting Institution

Kahramanmaraş Sütçü İmam Üniversitesi

Synthesis of Some New Carbazole-Metal Complexes and Their Thermal, Electronic, Spectral and Catalytic Alkene Oxidation Properties

Abstract

    Two new ligands [(E)-4-chloro-2-((9-ethyl-9H-carbazol-3-yl)methyleneamino)phenol, (E)-2-bromo-4-chloro-6-((9-ethyl-9H-carbazol-3-yl)methyleneamino)phenol] and their Cobalt (II), Manganese (II) and Nickel (II) complexes have been synthesized and characterized through various spectroscopic techniques (NMR, UV, IR, Mass etc.). Synthesized compounds have been examined for their catalytic activities in the oxidation reactions of styrene and cyclohexene. Manganese (II) complexes of both ligands showed the highest catalytic activity in alkene oxidations. Synthesized complex compounds proved that they could be used as catalysts in organic reactions requiring high temperatures. Electronic features of all the new compounds have also been reported for the first time with this paper.

Keywords

Catalysis, Complex, Schiffbase

References

• [1] Rayati, S., Salehi, F., Green oxidation of olefins and methyl phenyl sulfide with hydrogen peroxide catalyzed by an oxovanadium(IV) Schiff base complex encapsulated in the nanopores of zeolite-Y., Journal of Iranian Chemical Society, 12, 309-315, 2015.
• [2] Hassana, H.M.A., Saada, E.M., Soltana, M.S., Betiha, M.A., Butle, I.S., Mostafa, S.I., A palladium(II) 4-hydroxysalicylidene Schiff-base complex anchored on functionalized MCM-41: An efficient heterogeneous catalyst for the epoxidation of olefins, Applied Catalysis A-General, 488, 148-159, 2014.
• [3] Mavrogiorgoua, A., Papastergioua, M., Deligiannakis, Y., Louloudi, M., Activated carbon functionalized with Mn(II) Schiff base complexes as efficient alkene oxidation catalysts: Solid support matters, Journal Of Molecular Catalysis A-Chemical, 393, 8-17, 2014.
• [4] Maiti, M., Sadhukhan, D., Thakurta, S., Zangrando, E., Pilet, G., Signorella, S., Bellú, S., Mitra, S., Catalytic efficacy of copper(II) and cobalt(III) Schiff base complexes in aklene epoxidation, Bulletin of Chemical Society of Japan, 87, 724-732, 2014.
• [5] Shit, S., Saha, D., Saha, D., Row, T.N.G., Rizzoli, C., Azide/thiocyanate incorporated cobalt(III)-Schiff base complexes: Characterizations and catalytic activity in aerobic epoxidation of olefins, Inorganica Chimica Acta, 415, 103-110, 2014.
• [6] Heshmatpour, F., Rayati, S., Hajiabbas, M.A., Abdolalian, P., Neumüller, B., Copper(II) Schiff base complexes derived from 2,20 -dimethyl-propandiamine: Synthesis, characterization and catalytic performance in the oxidation of styrene and cyclooctene, Polyhedron, 31, 443-450, 2012. [7] Liu, D.F., Zhu, L.Q., Wu, J., Wu, L.Y., Lu, X.Q., Ring-opening copolymerization of epoxides and anhydrides using Manganese(III) asymmetrical Schiff base complex catalysts, RSC Advances, 5(5), 3854-3859, 2015.
• [8] Wu, L.Y., Fan, D.D., Lü, X.Q., Lu, R., Ring-opening Copolymerization of Cyclohexene Oxide and Maleic Anhydride Catalyzed by Mononuclear [Zn(L)(H2O)] or Binuclear [Zn2(L)(OAc)2(H2O)] Complex Based on the Salen-type Schiff-base Ligand, Chinese Journal of Polymmer Science, 32(6), 768-777, 2014.
• [9] Maleev, V.I., Chusov, D.A., Yashkina, L.V., Ikonnikov, N.S., II’in, M.M., Asymmetric ring opening of epoxides with cyanides catalysed by chiral binuclear titanium complexes, Tetrahedron-Asymmetry, 25, 838-843, 2014.
• [10] Bal, S., Bal, S.S., Cobalt(II) and Manganese(II) Complexes of NovelSchiff Bases, Synthesis, Characterization, and Thermal, Antimicrobial, Electronic, and Catalytic Features, Advances in Chemistry, 2014, 1-12, 2014.
• [11] Kadw, E., Bala, M.D., Friedrich, H.B., Characterisation and application of montmorillonite-supported Fe Schiff base complexes as catalysts for the oxidation of n-octane, Applied Clay Science, 95, 340-347, 2014.
• [12] Noshiranzadeh, N., Emami, M., Bikas, R., S´lepokura, K., Lis, T., Synthesis, characterization and catalytic reactivity of Mn(III) complexes with a scorpion-like bis(phenolate) ligand: Selective oxidation of primary alcohols to aldehydes, Polyhedron, 72, 56-65, 2014.
• [13] Wang, P., Dong, Z., Lei, Y., Du, Y., Li, H., Yang, H., Nie, Y., Ma, J., Highly selective oxidation of alcohols catalyzed by Cu(II)-Schiff base-SBA-15 with hydrogen peroxide in water, Journal of Porous Materials, 20, 277-284, 2013.
• [14] Das, A., Kureshy, R.I., Maity, N.Ch., Subramanian PS, Khan NH, R.Abdi SH, Suresh E, Bajaj HC. Synthesis and characterization of new chiral Cu(II)-N4 complexes and their application in the asymmetric aza-Henry reaction, Dalton Transactions, 43, 12357-12364, 2014.
• [15] Amirnasr, M., Bagheri, M., Farrokhpour, H., Schenk, K.J., Mereiter, K., Ford, P.C., New Zn(II) complexes with N2S2 Schiff base ligands. Experimental and theoretical studies of the role of Zn(II) in disulfide thiolate-exchange, Polyhedron, 71, 1-7, 2014.
• [16] Chandra, S., Vandana, K.S., Synthesis, spectroscopic, anticancer, antibacterial and antifungal studies of Ni(II) and Cu(II) complexes with hydrazine carboxamide, 2-[3-methyl-2-thienyl methylene], Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy., 135, 356-363, 2015.
• [17] Nagesh, G.Y., Raj, K.M., Mruthyunjayaswamy, B.H.M., Synthesis, characterization, thermal study and biological evaluation of Cu(II), Co(II), Ni(II) and Zn(II) complexes of Schiff base ligand containing thiazole moiety, Journal of Molecular Structure, 1079, 423-432, 2015.
• [18] Zhao, X.J., Xue, L.W., Zhang, C.X., Schiff Base Copper(II) and Zinc(II) Complexes: Synthesis, Structures, and Antimicrobial Activities, Synthesis and Reactivity in Inorganic Metal-Organic And Nano-Metal Chemistry, 45, 516-520, 2015.
• [19] Proetto, M., Liu, W., Hagenbach, A., Abram, U., Gust, R., Synthesis, characterization and in vitro antitumour activity of a series of novel platinum(II) complexes bearing Schiff base ligands, European Journal of Medicinal Chemistry, 53, 168-175, 2012.
• [20] Scozzafava, A., Menabuoni, L., Mincione, F., Mincione, G., Supuran, C.T., Carbonic anhydrase inhibitors: synthesis of sulphonamides incorporating dtpa tails and of their zinc complexes with powerful topical antiglaucoma properties, Bioorganic and Medicinal Chemistry Letters, 11(4), 575-582, 2001.
• [21] Scozzafava, A., Supuran, C.T., Carbonic Anhydrase and Matrix Metalloproteinase Inhibitors: Sulfonylated Amino Acid Hydroxamates with MMP Inhibitory Properties Act as Efficient Inhibitors of CA Isozymes I, II, and IV, and N-Hydroxysulfonamides Inhibit Both These Zinc Enzymes, Journal of Medicinal Chemistry, 43, 3677-3687, 2000.
• [22] Jiang, T., Wang, F., Tang, C., Zhang, X., Cao, X., Tao, Y., Huang, W., Carbazole/phenylpyridine hybrid compound as dual role of efficient hostand ligand of iridium complex: Well matching of host-dopant for solution-processed green phosphorescent OLEDs, Dyes Pigments, 150:130-138, 2018.
• [23] Ott, J.C, Blasius, C.K, Wadepohl, H., Gade, L.H., Synthesis, Characterization, and Reactivity of a High-Spin Iron(II) Hydrido Complex Supported by a PNP Pincer Ligand and Its Application as a Homogenous Catalyst for the Hydrogenation of Alkenes, Inorganic Chemistry, 57, 3183-3191, 2018.
• [24] Higuchi, J., Kuriyama, S., Eizawa, A., Arashiba, K., Nakajima, K., Nishibayashi, Y., Preparation and reactivity of iron complexes bearing anionic carbazole-based PNP-type pincer ligands toward catalytic nitrogen fixation, Dalton Transactions,;47, 1117-1121, 2018.
• [25] Yu, Z.-J., Chen, H., Lennox, A.J.J., Yan, L.-J., Liu, X.-F., Xu, D.-D., Chen, F., Xu, L.-X., Li, Y., Wu, Q.-A., Luo, S.-P., Heteroleptic copper(I) photosensitizers with carbazole-substitutedphenanthroline ligands: Synthesis, photophysical properties and applicationto photocatalytic H2 generation, Dyes and Pigments, 162, 771-775, 2019.
• [26] Yingjun, L., Nan, Z., Jihong, L., Kun, J., Siyuan, W., Detection of HSO4- Ion with a Colorimetric and Fluorescent Probe Based on Hydrolysis Reaction of Carbazole-Derived Schiff Base in Aqueous Medium, Chinese Journal of Organic Chemistry, 38, 3026-3031, 2018.
• [27] Zarnegaryan, A., Pahlevanneshan, Z., Moghadam, M., Tangestaninejad, S., Mirkhani, V., Mohammdpoor‑Baltork, I., Copper(II) Schiff base complex immobilized on graphene nanosheets: a heterogeneous catalyst for epoxidation of olefins, Jounal of Iranian Chemical Society, 16, 747-756, 2019.
• [28] Hazra, S., Rocha, B.G.M., Guedes da Silva, M.F.C., Karmakar, A., Pombeiro, A.J.L., Syntheses, Structures, and Catalytic Hydrocarbon Oxidation Properties of N-Heterocycle-Sulfonated Schiff Base Copper(II) Complexes, Inorganics, 7, 17, 2019.
• [29] Zakeri, H., Rayati, S., Zarei, G., Synthesis and characterization of a Mn‐Schiff base complex anchored on modified MCM‐41 as a novel and recyclable catalyst for oxidation of olefins, Applied Organomettalic Chemistry, 32, 4593, 2018.
• [30] Yoon, K.R., Ko, S-O, Lee, S.M., Lee, H., Synthesis and characterization of carbazole derived nonlinear optical dyes, Dyes and Pigments, 75, 567-573, 2007.
• [31] Grigoras, M., Antonoaia, N.-C., Synthesis and characterization of some carbazole-based imine polymers, European Polymer Journal, 41, 1079-1089, 2005.
• [32] Hester, R.E., Plane, R.A., Metal-Oxygen bonds in complexes: Raman spectra of trisacetylacetonato and trisoxalato complexes of Aluminum, Gallium and Indium, Inorganic Chemistry, 3, 513-517, 1964.
• [33] Finnie, K.S., Bartlett, J.R., Woolfrey, J.L., Vibrational Spectroscopic Study of the Coordination of (2,2'-Bipyridyl-4,4'-dicarboxylic acid)ruthenium(II) Complexes to the Surface of Nanocrystalline Titania, Langmuir, 14, 2744-2749, 1998.
• [34] Deacon, G.B., Phillips, R.J., Relationships Between the Carbon-Oxygen Stretching Frequencies of Carboxylato Complexes and The Type of Carboxylate Coordination, Coordination Chemistry Reviews, 33, 227-250, 1980.
• [35] Ispir, E., The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing schiff bases and their metal complexes, Dyes and Pigments, 82, 13-19, 2009.
• [36] Kurtoglu, M., Ispir, E., Kurtoglu, N., Toroglu, S., Serin, S., New soluble coordination chain polymers of nickel(II) and copper(II) ions and their biological activity, Transition Metal Chemistry, 30, 765-770, 2005.
• [37] Sawhney, K.J.S., Tiwari, M.K., Singh, A.K., Nandedkar'in, R.V., Joshi, S.K. et al. (Eds.). Proceedings of Sixth National Seminar on X-ray Spectroscopy and Allied Areas, pp. 130, 1998.
• [38] Tiwari, M.K., Singh, A.K., Sawhney, K.J., Analysis of stainless steel samples by energy dispersive X-ray fluorescence (EDXRF) spectrometry, Bulletin of Materials Science, 24, 633-638, 2001.
• [39] Roy, G.B., Synthesis and study of physico-chemical properties of a new chiral Schiff baseligand and its metal complex, Inorganica Chimica Acta, 362, 1709-1714, 2009.
• [40] El-Seıdy, A.M.A., In situ room temperature synthesis and characterization of salicylaldehyde phenylhydrazone metal complexes, their cytotoxic activity on MCF-7 cell line, and their ınvestigation as antibacterial and antifungal agents, Synthesis and Reactivity in Inorganic Metal-Organic And Nano-Metal Chemistry, 45, 437-446, 2015.
• [41] Shennar, K.A., Butcher, R.J., Greenaway, F.T., Co(II), Cu(II), Mn(II) and Ni(II) complexes of maleic hydrazide, Inorganica Chimica Acta, 425, 247-254, 2015.
• [42] Yang, Q., Lei, Y., Wang, P., Synthesis, X-Ray Structural Characterization, and Catalytic Property of a Manganese (II) Complex With 2-Bromo-6-[(3-cyclohexylammoniopropylimino)methyl]phenolate and Thiocyanate Ligands, Synthesis and Reactivity in Inorganic Metal-Organic And Nano-Metal Chemistry, 44, 1208-1211, 2014.
• [43] Bal, S., Orhan, B., Connolly, J.D., Digrak, M., Koytepe, S., Synthesis and characterization of some Schiff bases, their metal complexes and thermal, antimicrobial and catalytic features, Journal of Thermal Analysis And Calorimetry, 121, 909-917, 2015.
• [44] Mukherjee, S., Samanta, S., Roy, B.C., Bhaumik, A., Efficient allylic oxidation of cyclohexene catalyzed by immobilized Schiff base complex using peroxides as oxidants, Applıed Catalysis A-General, 301, 79-88, 2006.
• [45] Islam, S.M., Mondal, P., Mukherjee, S., Roy, A.S., Bhaumik, A., A reusable polymer anchored copper(II) complex catalyst for the efficient oxidation of olefins and aromatic alcohol, Polymers For Advanced Technologies, 22, 933-941, 2011.