Synthesis of axially di- and peripherally tetra-(4-{[(1E)-(4-methoxyphenyl)methylene]amino}phenoxy) group substituted metallophthalocyanines and their electrochemistry

Yıl 2023, Cilt: 5 Sayı: 2, 137 - 142, 29.12.2023

Hüseyin Baş Zekeriya Bıyıklıoğlu

https://doi.org/10.51435/turkjac.1381022

Öz

In this study, the new phthalonitrile derivative, axially di- and peripherally tetra-(4-{[(1E)-(4-methoxyphenyl)methylene]amino}phenoxy) group substituted metallophthalocyanines have been synthesized and characterized. Then electrochemical measurements of axially di- and peripherally tetra-(4-{[(1E)-(4-methoxyphenyl)methylene]amino}phenoxy) group substituted metallophthalocyanines were investigated with cyclic voltammogram (CV) technique. Phthalocyanine ring based redox processes are recorded owing to the redox inactivity of the Si4+, Cu2+ central cation of NP2-Si, NP2-Cu. NP2-Mn demonstrated both metal-based and Pc ring-based reduction processes, in contrast to NP2-Si and NP2-Cu.

Anahtar Kelimeler

Synthesis, Phthalocyanine, Silicon, Manganese, Cyclic voltammetry

Kaynakça

• N. Kayir, S. Gorduk, Synthesis, characterization, and investigation photophysicochemical properties of axially 2-hydroxymethyl-1,4-benzodioxan di-substituted Silicon(IV) phthalocyanine, J Organomet Chem, 990, 2023, 122661.
• R. Balamurugan, J.H. Liu, B.T. Liu, A review of recent developments in fluorescent sensors for the selective detection of palladium ions, Coord Chem Rev, 376, 2018, 196–224.
• T. Arslan, N. Çakır, T. Keleş, Z. Biyiklioglu, M. Senturk, Triazole substituted metal-free, metallo-phthalocyanines and their water soluble derivatives as potential cholinesterases inhibitors: Design, synthesis and in vitro inhibition study, Bioorg Chem, 90, 2019, 103100.
• S. Temizel, T.Ç. Çanak, A.M. Sevim, Novel polymers with cobalt(II)phthalocyanine moieties as effective heterogeneous photocatalysts for visible-light-driven photodegradation of organic dyes in aqueous solutions, J Photochem Photobiol A Chem, 401, 2020, 112741.
• R. Ishiura, A. Fujii, M. Arita, K. Sudoh, M. Ozaki, Study on energy level bending at heterojunction of solution-processed phthalocyanine thin film and n-Si by Kelvin probe force microscopy, Org Electron, 78, 2020, 105599.
• R. Zugle, T. Nyokong, Physico-chemical properties of lutetium phthalocyanine complexes in solution and in solid polystyrene polymer fibers and their application in photoconversion of 4-nitrophenol, J Mol Catal A Chem, 358, 2012, 49–57.
• M. Yahya, Y. Nural, Z. Seferoğlu, Recent advances in the nonlinear optical (NLO) properties of phthalocyanines: A review, Dye Pigment, 198, 2022, 109960.
• E. Güzel, H. Baş, Z. Biyiklioglu, İ. Şişman, Dye‐sensitized solar cells using silicon phthalocyanine photosensitizers with pyridine anchor: Preparation, evaluation of photophysical, electrochemical, and photovoltaic properties, Appl Organomet Chem, 35, 2021,.
• B. Yıldız, B.S. Arslan, E. Güzel, M. Nebioğlu, N. Menges, İ. Şişman, M. Kasım Şener, Non-aggregating zinc phthalocyanine sensitizer with bulky diphenylphenoxy donor groups and pyrazole-3-carboxylic acid anchoring group for coadsorbent-free dye-sensitized solar cells, Sol Energy, 226, 2021, 173–179.
• Z. Biyiklioglu, H. Bas, H. Alp, Non-aggregated axially disubstituted silicon phthalocyanines bearing electropolymerizable ligands and their aggregation, electropolymerizaton and thermal properties, Dalt Trans, 44, 2015, 14054–14062.
• Z. Biyiklioglu, H. Alp, Electropolymerizable peripherally tetra-{2-[3-(diethylamino)phenoxy]ethoxy} substituted as well as axially (4-phenylpiperazin-1-yl)propanoxy-disubstituted silicon phthalocyanines and their electrochemistry, Dalt Trans, 44, 2015, 18993–18999.
• Z. Biyiklioglu, I. Ömeroğlu, H. Alp, Synthesis, characterization and electrochemical properties of amphiphilic axially-disubstituted silicon(IV) phthalocyanines, J Coord Chem, 69, 2016, 354–362.
• Y. Baygu, Y. Gök, Synthesis and characterization of new partially-aggregated water-soluble polyether-triazole linked zinc(II) phthalocyanines as photosensitizers for PDT studies, Synth Met, 260, 2020, 116256.
• H. Kantekin, H. Yalazan, B. Barut, Ö. Güngör, D. Ünlüer, Ü. Demirbaş, A. Özel, M. Durmuş, Dual-purpose both peripheral and non-peripheral triazole substituted ZnII, MgII and PbII phthalocyanines: Synthesis, characterization, photophysicochemical and acetylcholinesterase inhibitory properties, Polyhedron, 208, 2021, 115416.
• A. Günsel, A.T. Bilgiçli, B. Barut, P. Taslimi, A. Özel, İ. Gülçin, Z. Biyiklioglu, M.N. Yarasir, Synthesis of water soluble tetra-substituted phthalocyanines: Investigation of DNA cleavage, cytotoxic effects and metabolic enzymes inhibition, J Mol Struct, 1214, 2020, 128210.
• Z. Bıyıklıoğlu, V. Çakır, D. Çakır, H. Kantekin, Crown ether-substituted water soluble phthalocyanines and their aggregation, electrochemical studies, J Organomet Chem, 749, 2014, 18–25.
• R. Atajanov, B. Huraibat, Z. Odabaş, A.R. Özkaya, Electrochemical, spectroelectrochemical, and electrocatalytic properties of novel soluble phthalocyanines containing peripheral thymoxy and chloride units, Inorganica Chim Acta, 547, 2023, 121360.
• H. Baş, Z. Biyiklioglu, B. Barut, C.Ö. Yalçın, A. Özel, Highly water soluble axial disubstituted silicon(IV) phthalocyanine, naphthalocyanine: Synthesis, DNA interaction and anticancer effects against human lung (A549), liver (SNU-398), melanoma (SK-MEL128), prostate (DU-145), breast (BT-20) cell lines, Inorg Chem Commun, 156, 2023, 111139.
• A. Günsel, P. Taslimi, G.Y. Atmaca, A.T. Bilgiçli, H. Pişkin, Y. Ceylan, A. Erdoğmuş, M.N. Yarasir, İ. Gülçin, Novel potential metabolic enzymes inhibitor, photosensitizer and antibacterial agents based on water-soluble phthalocyanine bearing imidazole derivative, J Mol Struct, 1237, 2021, 130402.
• S.M. Sudhakara, M.C. Devendrachari, F. Khan, S. Thippeshappa, H.M.N. Kotresh, Highly sensitive and selective detection of nitrite by polyaniline linked tetra amino cobalt (II) phthalocyanine surface functionalized ZnO hybrid electrocatalyst, Surfaces and Interfaces, 36, 2023, 102565.
• R.A. Shoukat Ali, J. Keshavayya, A.S. Jagadisha, S.D. Umesha, K.N. Gujjar, S.A. Narasimha, D.G. Prasanna, E. Nagaraja, DC electrical conductivity studies of tetra 2-(furan-2-yl)-1,3,4-oxadiazole substituted metal (II) phthalocyanines, Mater Today Proc, 49, 2022, 644–649.
• M.-R. Ke, J.-D. Huang, S.-M. Weng, Comparison between non-peripherally and peripherally tetra-substituted zinc (II) phthalocyanines as photosensitizers: Synthesis, spectroscopic, photochemical and photobiological properties, J Photochem Photobiol A Chem, 201, 2009, 23–31.
• D. AlMarzouq, S. A. Majeed, Ö. Budak, A. Koca, Manganese phthalocyanine and its graphene quantum dot conjugate: Synthesis, characterization electrochemistry, spectroelectrochemistry, electropolymerization, and electrochromism, Inorganica Chim Acta, 527, 2021, 120558.
• Y. Ünver, H. Baş, Z. Biyiklioglu, Non-peripherally 4-{[(1E)-1-benzothien-2-ylmethylene]amino}phenol substituted zinc(II), manganese(III), cobalt(II) phthalocyanines: Synthesis and electrochemistry, J Mol Struct, 1178, 2019, 508–513.
• S. Gorduk, A. Altindal, Non-peripherally tetra substituted phthalocyanines bearing carboxylic acid anchoring groups as photosensitizer for high efficient dye-sensitized solar cells, J Mol Struct, 1204, 2020, 127636.
• S. Gorduk, Investigation of photophysicochemical properties of non-peripherally tetra-substituted metal-free, Mg(II), Zn(II) and In(III)CI phthalocyanines, Polyhedron, 189, 2020, 114727.
• R. Bayrak, H.T. Akçay, Z. Bıyıklıoğlu, İ. Değirmencioğlu, Substituted phthalocyanines and their electropolymerization properties, Synth Met, 220, 2016, 643–652.
• M. Shumba, T. Nyokong, Electrode modification using nanocomposites of boron or nitrogen doped graphene oxide and cobalt (II) tetra aminophenoxy phthalocyanine nanoparticles, Electrochim Acta, 196, 2016, 457–469.
• Ö. Kurt, A. Koca, A. Gül, M. Burkut Koçak, Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups, Synth Met, 206, 2015, 72–83.
• A. Günsel, M. Kandaz, A. Koca, B. Salih, Peripheral and non-peripheral-designed multifunctional phthalocyanines; synthesis, electrochemistry, spectroelectrochemistry and metal ion binding studies, Polyhedron, 30, 2011, 1446–1455.
• G.H. Hegazy, H.I. Ali, Design, synthesis, biological evaluation, and comparative Cox1 and Cox2 docking of p-substituted benzylidenamino phenyl esters of ibuprofenic and mefenamic acids, Bioorg Med Chem, 20, 2012, 1259–1270.
• H. Fazlı, Ç. Akkol, S.C. Osmanoğulları, Z. Biyiklioglu, E.T. Saka, O. Bekircan, Synthesis of water soluble copper(II), manganese(III) phthalocyanines and their photocatalytic performances in benzyl alcohol photoxidation, J Organomet Chem, 983, 2023, 122553.
• Z. BIYIKLIOĞLU, H. BAŞ, Synthesis and effect of substituent position, metal type on the electrochemical properties of (3-morpholin-4-ylpropoxy) groups substituted cobalt, manganese phthalocyanines, TURKISH J Chem, 44, 2020, 687–694.
• G. Gümrükçü Köse, G.K. Karaoğlan, Y. Erdağ Maden, A. Koca, Novel silicon phthalocyanine photosensitizers containing carboxylic acid based axial anchoring groups: Electrochemistry, spectroelectrochemistry, and dye sensitized solar cell performance, Dye Pigment, 207, 2022, 110686.
• H. Yalazan, Y.E. Maden, A. Koca, H. Kantekin, Multi-step syntheses, electrochemistry and spectroelectrochemistry of peripheral CoII, CuII and MnIIICl phthalocyanines bearing pyrazoline, J Mol Struct, 1269, 2022, 133788.
• D. Akyüz, Ü. Demirbaş, O. Bekircan, Metallo‐phthalocyanines Containing 1,3,4‐oxadiazole Substituents: Synthesis, Characterization, Electrochemical and Spectroelectrochemical Properties, ChemistrySelect, 8, 2023, e20220459.
• G. Dilber, A. Nas, Ö. Budak, A. Koca, Chloromanganese and oxo-Titanium (IV) phthalocyanines: Synthesis, electrochemistry and Spectroelectrochemistry, Polyhedron, 242, 2023, 116495.