Novel indium(III) acetate phthalocyanine: synthesis and spectroscopic properties

Year 2022, Volume: 10 Issue: 1, 81 - 87, 30.06.2022

Berra Gülem Gökçe , Hüseyin Kenan Soylu , Emir Gürel , Merve Cengiz , Fatih Mutlu , Mehmet Pişkin

https://doi.org/10.51354/mjen.1076925

Abstract

A new phthalocyanine 1 was synthesized, containing 2-aminophenoxy groups as tetra from its peripheral positions and indium(III) acetate in its cavity. The structure of 1 was illuminated by elemental analysis, FTIR, UV-vis and fluorescence spectroscopy techniques It is well soluble in solvents such as polar and nonpolar solvent types. Its aggregation properties have been studied both in the solvents mentioned above and in Dimethyl sulfoxide at different concentrations. Its aggregation properties were examined in these solvents as well as in Dimethyl sulfoxide at certain different concentration ranges. With these determined spectroscopic properties, it can be a candidate for use in various technological applications.

Keywords

Phthalocyanine , indium(III) acetate , 2-aminophenol , spectroscopic , fluorescence

References

• McKeown N.B., “Phthalocyanine Materials; Synthesis, Structure and Function” Cambridge University Press, (1998), Cambridge, 197.
• Pişkin M., Odabaş Z., “Synthesis, Characterization and Spectroscopic Properties of Novel Mono-Lutetium(III) Phthalocyanines”, Karaelmas Science and Engineering Journal, 6(2), (2016), 307-314.
• Pişkin M., Özturk Ö.F., Odabaş Z., “Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine”, Manas Journal of Engineering, 9 (1), (2021), 58-64.
• Pişkin M., Özturk Ö.F., Odabaş Z., “Newly Soluble and Non-Aggregated Copper(II) and Tin(II) Phthalocyanines: Synthesis, Characterization and Investigation of Photophysical and Photochemical- Responsive”, Karaelmas Science and Engineering Journal, 7(2), (2017), 627-637.
• Demirbaş Ü., Pişkin M., Barut B., Bayrak R., Durmuş M., Kantekin H., “Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3-(2H-benzo[d][1,2,3] triazol-2-yl)-4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties”, Synthetic Metals, 220, (2016), 276–285.
• Çetinkaya M., Pişkin M., Altun, S., Odabaş Z., Durmuş M., “Do the positions of trimethyl groups on phthalocyanine photosensitizers improve their photochemical and photophysical properties?”, Journal of Photochemistry and Photobiology A: Chemistry, 335, (2017), 17–25.
• Demirbaş Ü., Pişkin M., Bayrak R., Durmuş M., Kantekin H., “Zinc(II) and lead(II) phthalocyanines bearing thiadiazole substituents: Synthesis, characterization, photophysical and photochemical properties”, Journal of Molecular Structure, 1197, (2019), 594-602.
• Makhseed S., Al-Sawah M., Samuel J., Mana H., “Synthesis, characterization and nonlinear optical properties of nonaggregating hexadeca-substituted phthalocyanines”, Tetrahedron Lett., 50, (2009), 165.
• Mutlu F., Pişkin M., Canpolat E., Öztürk Ö.F., "The new zinc(II) phthalocyanine directly conjugated with 4-butylmorpholine units: Synthesis, characterization, thermal, spectroscopic and photophysical properties", Journal of Molecular Structure, 1201, (2020), 127169.
• Pişkin M., Öztürk N., Durmuş M., “Spectroscopic and electrochemical behavior of the novel tetra-2-methyl-pyrazinoporphyrazines”, Journal of Molecular Structure, 1149 (2017) 893-899.
• Orman E.B., Pişkin M., Odabaş Z., Özkaya A.R., “Electrochemical, Spectroelectrochemical, and Electrocatalytic Dioxygen Reducing Properties of Peripheral Tetra-2,6-dimethoxyphenoxy Substituted Phthalocyanines”, Electroanalysis 33, (2021), 2310–2322.
• Pişkin M., Can Nursel, Odabaş Z., Altındal A., “Toluene vapor sensing characteristics of novel copper(II),indium(III), mono-lutetium(III) and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenoxy bioactive moieties, Journal of Porphyrins and Phthalocyanines, 22, (2018), 1–9.
• Yazıcı A., Dalbul N., Altındal A., Salih B., Bekaroğlu Ö., “Ethanol sensing property of novel phthalocyanines substituted with 3,4-dihydroxy-3-cyclobuten-1,2-dione”, Sensors and Actuators B., 202, (2014), 14–22.
• Mert S.A., Ilgün C., Gül A., “Preparation of heterogeneous phthalocyanine catalysts by cotton fabric dyeing”, Dyes and Pigments, 89, (2011), 162–168.
• Akçay H.T., Pişkin M., Demirbaş Ü., Bayrak R., Durmuş M., Menteşe E., Kantekin H., “Novel triazole bearing zinc(II) and magnesium(II) metallo-phthalocyanines: Synthesis, characterization, photophysical and photochemical properties”, Journal of Organometallic Chemistry, 745 (746), (2013), 379-386.
• Soylu M., Ocaya R., Tuncer H., Al-Ghamdi A.A., Dere A., Sari D.C., Yakuphanoglu F., “Analysis of photovoltaic behavior of Si-based junctions containing novel graphene oxide/nickel (II) phthalocyanine composite films”, Microelectronic Engineering, 154, (2016), 53–61.
• Kantekin H., Yalazan H., Kahriman N., Ertem B., Serdaroğlu V., Pişkin M., Durmuş M.,“New peripherally and non-peripherally tetra-substituted metal-free, magnesium(II) and zinc(II) phthalocyanine derivatives fused chalcone units: Design, synthesis, spectroscopic characterization, photochemistry and photophysics”, Journal of Photochemistry and Photobiology A: Chemistry, 361, (2018), 1-11.
• Lino H., Hanna J., Bushby R.J., Movaghar B., Whitaker B.J., Cook M.J., “Very high time-of-flight mobility in the columnar phases of a discotic liquid crystal”, Applied Physics Letters, 87, (2005), 132102.
• Bayrak R., Akçay H.T., Pişkin M., Demirbaş Ü., Durmuş M., Değirmencioğlu İ., “Azine-bridged binuclear metallophthalocyanines functioning photophysical and photochemical-responsive”, Dyes and Pigments 95, (2012), 330-337.
• Dong S., Tian H., Huang L., Zhang J., Yan D., Geng Y., Wang F., “Non‐Peripheral Tetrahexyl‐Substituted Vanadyl Phthalocyanines with Intermolecular Cofacial π–π Stacking for Solution‐Processed Organic Field‐Effect Transistors”, Advanced Materials, 23, (2011), 2850–2854.
• Lu G., Kong X., Sun J., Zhang L., Chen Y., Jiang J., “Solution-processed single crystal microsheets of a novel dimeric phthalocyanine-involved triple-decker for high-performance ambipolar organic field effect transistors”, Chemical Communications, 53, (2017), 12754–12757.
• Demirbaş Ü., Bayrak R., Pişkin M., Akçay H.T., Durmuş M., Kantekin H., “Synthesis, photophysical and photochemical properties of novel tetra substituted metal free and metallophthalocyanines bearing triazine units” Journal of Organometallic Chemistry, 724, (2013), 225-234.
• Ramya E., Momen N., Rao D.N., “Preparation of multiwall carbon nanotubes with zinc phthalocyanine hybrid materials and their nonlinear optical (NLO) properties”, Journal of Nanoscience and Nanotechnology, 18 (7), (2018), 4764–4770.
• Ghanem B.S., Pişkin M., Durmuş M., El-Khouly M.E., Al-Raqa S.Y., “Synthesis, photophysical and photochemical properties of novel phthalocyanines substituted with triptycene moieties”, Polyhedron, 90, (2015), 85–90.
• Al-Sohaimi B.R., Pişkin M., Ghanem B.S., Al-Raqa S.Y., Durmuş M., “Efficient singlet oxygen generation by triptycene substituted A3B type zinc(II) phthalocyanine photosensitizers”, Tetrahedron Letters, 57, (2016) , 300–304.
• Zheng L., Xu J., Feng Y., Shan H., Fang G., Xu Z.X., “Green solvent processed tetramethyl-substituted aluminum phthalocyanine thin films as anode buffer layers in organic light-emitting diodes”, Journal of Materials Chemistry C, 6, (2018), 11471–11478.
• Al-Sohaimi B.R., Pişkin M., Aljuhani A., Al-Raqa S.Y., Durmuş M.,“Enhancing photophysical and photochemical properties of zinc(II) Phthalocyanine dyes by substitution of triptycene moieties”, Journal of Luminescence,173, (2016), 82–88.
• Kumar A., Punia R., Gupta A.K., Mohan D., Kapoor K., “Study of all-optical switching properties of zinc phthalocyanine thin film by pump-probe technique”, Optics & Laser Technology, 95, (2017), 100–104.
• Pişkin M., “Synthesis, characterization, thermal and photophysical properties of novel strontium (II) phthalocyanine”, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 102, (2022), 35–44.
• Pişkin M., Öztürk Ö.F., Odabaş Z., “Determination of photophysical, photochemical and spectroscopic properties of novel lead(II) phthalocyanines”, Polyhedron, 182, (2020), 114480.
• Sfyri G., Vamshikrishn N., Kumar C.V., Giribabu L., Lianos P.,” Synthesis and characterization of tetratriphenylamine Zn phthalocyanine as hole transporting material for perovskite solar cells”, Solar Energy, 140, (2016), 60–65.
• Nas A., Demirbaş Ü., Pişkin M., Durmuş M., Kantekin H., “The photophysical and photochemical properties of new unmetallated and metalated phthalocyanines bearing four 5-chloroquinolin-8-yloxy substituents on peripheral sites”, Journal of Luminescence, 145, (2014), 635–642.
• Jia Y., Li J., Chen J., Hu P., Jiang L., Chen X., Huang M., Chen Z., Xu P., “Smart photosensitizer: tumor-triggered oncotherapy by self-assembly photodynamic nanodots”, ACS Applied Materials & Interfaces, 10, (2018), 15369–15380.
• Pişkin M., Durmuş M., Bulut M., “Highly soluble 7-oxy-3-(4-methoxyphenyl) coumarin bearing zinc phthalocyanines: Synthesis and investigation of photophysical and photochemical properties”, Journal of Photochemistry and Photobiology A: Chemistry, 223, (2011), 37– 49.
• Pişkin M., Durmuş M., Bulut M., “Synthesis and investigation on photophysical and photochemical properties of 7-oxy-3-methyl-4-phenylcoumarin bearing zinc phthalocyanines”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, (2012), 502–511.
• Çakır V. Çakır D., Pişkin M., Durmuş M., Bıyıklıoğlu Z., “Water soluble peripheral and non-peripheral tetra substituted zinc phthalocyanines: Synthesis, photochemistry and bovine serum albumin binding behavior”, Journal of Luminescence, 154, (2014), 274–284.
• Çakır V. Çakır D., Pişkin M., Durmuş M., Bıyıklıoğlu Z., “New peripherally and non-peripherally tetra-substituted water-soluble zinc phthalocyanines: Synthesis, photophysics and photochemistry”, Journal of Organometallic Chemistry, 783, (2015), 120-129.
• Aktaş A., Pişkin M., Durmuş M., Bıyıklıoğlu Z., “Synthesis, photophysical and photochemical properties of zinc phthalocyanines bearing fluoro-functionalized substituents”, Journal of Luminescence, 145, (2014), 899–906.
• Şahal H., Pişkin, M., Organ G.A., Öztürk Ö.F., Kaya M., Canpolat E., "Zinc(II) phthalocyanine containing Schiff base containing sulfonamide: synthesis, characterization, photophysical, and photochemical properties", Journal of Coordination Chemistry, 71 (22), (2018), 3763–3775.
• Pişkin, M., Canpolat E., Öztürk Ö.F., “The new zinc phthalocyanine having high singlet oxygen quantum yield substituted with new benzenesulfonamide derivative groups containing schiff base”, Journal of Molecular Structure, 1202, (2020), 127181.
• Demirbaş Ü., Pişkin M., Bayrak R., Ünlüer D., Düğdü E., Durmuş M., Kantekin H., “The determination of photophysical and photochemical parameters of novel metal-free, zinc(II) and lead(II) phthalocyanines bearing 1,2,4-triazole groups”, Synthetic Metals, 219, (2016), 76–82.
• Gargiani P., Rossi G., Biagi R., Corradini V., Pedio M., Fortuna S., Calzolari A., Fabris S., Cezar J.C., Brookes N.B., Betti M.G., “Spin and orbital configuration of metal phthalocyanine chains assembled on the Au(110) surface”, Physical Review B Covering Condensed Matter and Materials Physics, 87, (2013), 165407.
• Demirbaş Ü., Pişkin M., Akçay H.T., Barut B., Durmuş M., Kantekin H., “Synthesis, characterisation, photophysical and photochemical properties of free-base tetra-(5-chloro-2-(2,4-dichlorophenoxy)phenoxy)phthalocyanine and respective zinc(II) and lead(II) complexes”, Synthetic Metals, 223, (2017), 166–171.
• Pişkin M., “The novel 2,6-dimethoxyphenoxy substituted phthalocyanine dyes having high singlet oxygen quantum yields”, Polyhedron, 104, (2016), 17-24.
• Gürel E, Pişkin M., Altun S., Odabaş Z., Durmuş M., “Synthesis, characterization and investigation of the photophysical and photochemical properties of highly soluble novel metal-free, zinc(II), and indium(III) phthalocyanines substituted with 2,3,6-trimethylphenoxy moieties”, Dalton Transactions, 44, (2015), 6202–6211.
• Gürel E, Pişkin M., Altun S., Odabaş Z., Durmuş M., “The novel mesityloxy substituted metallo-phthalocyanine dyes with long fluorescence lifetimes and high singlet oxygen quantum yields”, Journal of Photochemistry and Photobiology A: Chemistry, 315, (2016), 42–51.
• Çapkın A., Pişkin M., Durmuş M., Bulut M., “Spectroscopic, photophysical and photochemical properties of newly metallo-phthalocyanines containing coumarin derivative”, Journal of Molecular Structure 1213 (2020) 128145.
• Pişkin M., Durmuş M., Bulut M., “Synthesis, characterization, photophysical and photochemical properties of 7-oxy-3-methyl-4-phenylcoumarin-substituted indium phthalocyanines”, Inorganica Chimica Acta, 373, (2011), 107–116.
• Pişkin M., Altun S., Durmuş M., Odabaş Z., “First investigation on the photophysical and photochemical properties of azo-bridged phthalocyanine photosensitizers”, Journal of Luminescence,180, (2016), 219–223.
• Alamin Ali H.E., Pişkin M., Altun S., Durmuş M., Odabaş Z., “Synthesis, characterization, photophysical, and photochemical properties of novel zinc(II) and indium(III) phthalocyanines containing 2-phenylphenoxy units”, Journal of Luminescence,173, (2016), 113–119.
• Watson D.C., Hill A.E., “Aminophenols”. In Ullmann's Encyclopedia of Industrial Chemistry (2017), Wiley-VCH Verlag, 3, 59-77.