SavedAdd your journal

Journals / Sakarya University Journal of Science / 2026 / Volume: 30 Issue: 4

Chalcone-Appended Metallophthalocyanines: Synthesis, Redox Properties, and Catalytic Oxidation of 2-Mercaptoethanol

Hüseyin Karaca(Sakarya Üniversitesi Fen Fakültesi)0000-0003-2636-5836
Özlem Güven0000-0000-0000-0000
M. Dinesh Kumar(Dr. N.G.P. Arts and Science College)0000-0000-0000-0001
Ravikumar Raju(Dr. N.G.P. Arts and Science College)0000-0000-0000-0002
Pages
—
Publication Date
2026-08-29
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

These results highlight the potential of chalcone-functionalized phthalocyanines, especially Pc-7, as robust redox-active and catalytic materials.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:A novel series of metallophthalocyanines (M = Zn, Co, Cd), each bearing four peripheral chalcone groups, was synthesized and its characterization was carried out through FT-IR, NMR (¹H and ¹³C), HRMS, UV-Vis spectroscopy.
📊
Key Findings & Data:Notably, Pc-6 underwent non-reversible reduction (−0.86 V) and oxidation (0.20 V), while Pc-7 and Pc-8 showed reversible reductions at −0.65 V and −0.64 V, respectively.
💡
Conclusion & Impact:These results highlight the potential of chalcone-functionalized phthalocyanines, especially Pc-7, as robust redox-active and catalytic materials.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Chalcone · Phthalocyanine · Redox

Abstract

A novel series of metallophthalocyanines (M = Zn, Co, Cd), each bearing four peripheral chalcone groups, was synthesized and its characterization was carried out through FT-IR, NMR (¹H and ¹³C), HRMS, UV-Vis spectroscopy. Electrochemical investigations revealed distinctive redox behaviors for each complex. Notably, Pc-6 underwent non-reversible reduction (−0.86 V) and oxidation (0.20 V), while Pc-7 and Pc-8 showed reversible reductions at −0.65 V and −0.64 V, respectively. Spectroelectrochemical analysis indicated that Pc-6 and Pc-8 rapidly decomposed following ring-based redox events, whereas Pc-7 displayed a more stable and dynamic transformation, characterized by distinct isosbestic points and the emergence of new absorption bands. This behavior underscores the enhanced electronic delocalization and redox stability of Pc-7. Furthermore, Pc-7 demonstrated catalytic activity in the oxidation of 2-mercaptoethanol, yielding a turnover number of 45.84 and an initial rate of 0.084 µmol·s⁻¹. These results highlight the potential of chalcone-functionalized phthalocyanines, especially Pc-7, as robust redox-active and catalytic materials.

🔖

Cite This Article

Karaca, H., Güven, Ö., Kumar, M. D., Raju, R. (2026). Chalcone-Appended Metallophthalocyanines: Synthesis, Redox Properties, and Catalytic Oxidation of 2-Mercaptoethanol. Sakarya University Journal of Science, Volume: 30 Issue: 4. https://doi.org/10.16984/saufenbilder.1786927

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (87)

  1. G. Güney and S. Gördük, “Photophysical and photochemical studies on non-peripherally and peripherally Ga(III) chloro phthalocyanines in different solvents,” J. Organomet. Chem., vol. 999, Art. no. 122813, 2023, doi: 10.1016/j.jorganchem.2023.122813.
  2. L. Hu, H. Han, Z. Xu, K. Song, and F. Wang, “Synthesis, photophysical, and photochemical properties of functional molecules based on a novel zinc(II) phthalocyanine-1,8-naphthalimide skeleton,” J. Mol. Struct., vol. 1291, Art. no. 136007, 2023, doi: 10.1016/j.molstruc.2023.136007.
  3. R. Zugle, C. Litwinski, and T. Nyokong, “Photophysical characterization of dysprosium, erbium and lutetium phthalocyanines tetrasubstituted with phenoxy groups at non-peripheral positions,” Polyhedron, vol. 30, no. 9, pp. 1612–1619, 2011, doi: 10.1016/j.poly.2011.03.030.
  4. A. M. Sevim, C. Ilgün, and A. Gül, “Preparation of heterogeneous phthalocyanine catalysts by cotton fabric dyeing,” Dyes Pigments, vol. 89, no. 2, pp. 162–168, 2011, doi: 10.1016/j.dyepig.2010.10.008.
  5. E. Güzel et al., “Zinc and chloroindium complexes of furan-2-ylmethoxy substituted phthalocyanines: Preparation and investigation of aggregation, singlet oxygen generation, antioxidant and antimicrobial properties,” Synth. Met., vol. 245, pp. 127–134, 2018, doi: 10.1016/j.synthmet.2018.08.018.
  6. A. Günsel, E. Güzel, A. T. Bilgiçli, İ. Şişman, and M. N. Yaraşır, “Synthesis of non-peripheral thioanisole-substituted phthalocyanines: Photophysical, electrochemical, photovoltaic, and sensing properties,” J. Photochem. Photobiol. A Chem., vol. 348, pp. 57–67, 2017, doi: 10.1016/j.jphotochem.2017.07.040.
  7. D. G. Solğun and M. S. Ağırtaş, “Synthesis of novel an axially substituted silicon phthalocyanine and determination of its selectivity for Fe³⁺,” J. Mol. Struct., vol. 1286, Art. no. 135577, 2023, doi: 10.1016/j.molstruc.2023.135577.
  8. M. S. Ağırtaş, D. G. Solğun, B. Savaş, and T. Öztürk, “Synthesis and sensor properties of silicon phthalocyanine axially substituted with bis(prop-2-ynyloxy) groups and polymeric phthalocyanines bearing PEG substituent by ‘click’ chemistry,” Polycycl. Aromat. Compd., vol. 43, no. 4, pp. 3278–3290, 2023, doi: 10.1080/10406638.2022.2067195.
  9. H. Karaca, M. Teker, and A. Gül, “Catalytic oxidation of 2-mercaptoethanol by a water-soluble porhphyrazinatocobalt(II) complex,” Chem. J., vol. 6, no. 1, pp. 55–58, 2016.
  10. H. Karaca, N. Akçay, and M. Teker, “Porphyrazine immobilization on polyester fabric and heterogeneous catalytic application on oxidation of 2-mercaptoethanol,” Fresenius Environ. Bull., vol. 25, no. 5, pp. 1714–1718, 2016.
  11. J. P. Mensing, A. Wisitsoraat, A. Tuantranont, and T. Kerdcharoen, “Inkjet-printed sol–gel films containing metal phthalocyanines/porphyrins for opto-electronic nose applications,” Sens. Actuators B Chem., vol. 176, pp. 428–436, 2013, doi: 10.1016/j.snb.2012.09.053.
  12. M. Gay-Martín, E. Díez-Arévalo, M. L. Rodríguez-Méndez, and J. A. de Saja Sáez, “Electrochemical quartz crystal microbalance analysis of the oxidation reaction of phenols found in wines at lutetium bisphthalocyanine electrodes,” Sens. Actuators B Chem., vol. 185, pp. 24–31, 2013, doi: 10.1016/j.snb.2013.04.115.
  13. K. B. Manjunatha, R. Dileep, G. Umesh, and B. R. Bhat, “Nonlinear optical and all-optical switching studies of novel ruthenium complex,” Opt. Laser Technol., vol. 52, pp. 103–108, 2013, doi: 10.1016/j.optlastec.2013.04.019.
  14. S. Gördük, O. Avcıata, and U. Avcıata, “Photocatalytic degradation of methylene blue under visible light irradiation by non-peripherally tetra-substituted phthalocyanine–TiO₂ nanocomposites,” Inorg. Chim. Acta, vol. 471, pp. 137–147, 2018, doi: 10.1016/j.ica.2017.11.004.
  15. L. Grządziel and M. Krzywiecki, “Quantitative correlation between air-induced changes of electronic parameters and morphological features of copper phthalocyanine thin-film surfaces,” Mater. Chem. Phys., vols. 149–150, pp. 574–581, 2015, doi: 10.1016/j.matchemphys.2014.11.008.
  16. G. K. Kantar, N. Baltaş, E. Menteşe, and S. Şaşmaz, “Microwave-assisted synthesis and investigation of xanthine oxidase inhibition of new phthalonitrile and phthalocyanines containing morpholino-substituted 1,2,4-triazole-3-one,” J. Organomet. Chem., vol. 787, pp. 8–13, 2015, doi: 10.1016/j.jorganchem.2015.03.033.
  17. R. A. Shoukat Ali et al., “DC electrical conductivity studies of tetra 2-(furan-2-yl)-1,3,4-oxadiazole substituted metal(II) phthalocyanines,” Mater. Today Proc., vol. 49, pt. 3, pp. 644–649, 2022, doi: 10.1016/j.matpr.2021.05.163.
  18. A. Kumar, R. Meunier-Prest, F. Herbst, O. Heintz, E. Lesniewska, and M. Bouvet, “Covalent grafting of aryls to modulate the electrical properties of phthalocyanine-based heterostructures: Application to ammonia sensing,” Chem. Eng. J., vol. 436, Art. no. 135207, 2022, doi: 10.1016/j.cej.2022.135207.
  19. A. Kumar, G. Zhang, W. Liu, and X. Sun, “Electrocatalysis and activity descriptors with metal phthalocyanines for energy conversion reactions,” J. Electroanal. Chem., vol. 922, Art. no. 116799, 2022, doi: 10.1016/j.jelechem.2022.116799.
  20. S. Abdel Aal and D. Awadh, “The effect of anchoring group on the performances of metal-free phthalocyanine and metallophthalocyanine dye/titanium dioxide interface for dye-sensitized solar cells,” Surf. Interfaces, vol. 32, Art. no. 102089, 2022, doi: 10.1016/j.surfin.2022.102089.
  21. H. Sarıoğulları, I. F. Şengül, and A. G. Gürek, “Comparative study on sensing and optical properties of carbazole-linked novel zinc(II) and cobalt(II) phthalocyanines,” Polyhedron, vol. 227, Art. no. 116139, 2022, doi: 10.1016/j.poly.2022.116139.
  22. S. Zhang et al., “Interface engineering via phthalocyanine decoration of perovskite solar cells with high efficiency and stability,” J. Power Sources, vol. 438, Art. no. 226987, 2019, doi: 10.1016/j.jpowsour.2019.226987.
  23. M. Chaabene, B. Gassoumi, P. Mignon, R. Ben Chaâbane, and A. R. Allouche, “New zinc phthalocyanine derivatives for nitrogen dioxide sensors: A theoretical optoelectronic investigation,” J. Mol. Graph. Model., vol. 88, pp. 174–182, 2019, doi: 10.1016/j.jmgm.2019.01.008.
  24. A. L. Uğur, A. Erdoğmuş, A. Koca, and U. Avcıata, “Synthesis, spectroscopic, electrochemical and spectroelectrochemical properties of metal-free, manganese, and cobalt phthalocyanines bearing peripherally octakis[4-(thiophen-3-yl)phenoxy] substituents,” Polyhedron, vol. 29, no. 18, pp. 3310–3317, 2010, doi: 101016/j.poly.2010.09.008.
  25. A. A. Ensafi and H. Karimi-Maleh, “Modified multiwall carbon nanotubes paste electrode as a sensor for simultaneous determination of 6-thioguanine and folic acid using ferrocenedicarboxylic acid as a mediator,” J. Electroanal. Chem., vol. 640, nos. 1–2, pp. 75–83, 2010, doi: 10.1016/j.jelechem.2010.01.010.
  26. H. N. Raval, D. S. Sutar, and V. R. Rao, “Copper(II) phthalocyanine-based organic electronic devices for ionizing radiation dosimetry applications,” Org. Electron., vol. 14, no. 5, pp. 1281–1290, 2013, doi: 10.1016/j.orgel.2013.02.026.
  27. H. Mizuseki, N. Igarashi, R. V. Belosludov, A. A. Farajian, and Y. Kawazoe, “Theoretical study of phthalocyanine–fullerene complex for a high-efficiency photovoltaic device using ab initio electronic structure calculation,” Synth. Met., vol. 138, nos. 1–2, pp. 281–283, 2003, doi: 10.1016/S0379-6779(02)01289-4.
  28. Z. Şahin, R. Meunier-Prest, F. Dumoulin, A. Kumar, Ü. İşci, and M. Bouvet, “Tuning of organic heterojunction conductivity by the substituents’ electronic effects in phthalocyanines for ambipolar gas sensors,” Sens. Actuators B Chem., vol. 332, Art. no. 129505, 2021, doi: 10.1016/j.snb.2021.129505.
  29. E. Yabaş, E. Biçer, and A. Altındal, “Novel reduced graphene oxide/zinc phthalocyanine and reduced graphene oxide/cobalt phthalocyanine hybrids as high-sensitivity room-temperature volatile organic compound gas sensors,” J. Mol. Struct., vol. 1271, Art. no. 134076, 2023, doi: 10.1016/j.molstruc.2022.134076.
  30. S. Gai, B. Wang, X. Wang, R. Zhang, S. Miao, and Y. Wu, “Ultrafast NH₃ gas sensor based on phthalocyanine-optimized non-covalent hybrid of carbon nanotubes with pyrrole,” Sens. Actuators B Chem., vol. 357, Art. no. 131352, 2022, doi: 10.1016/j.snb.2021.131352.
  31. T. Miyata, S. Kawaguchi, M. Ishii, and T. Minami, “High-sensitivity chlorine gas sensors using Cu–phthalocyanine thin films,” Thin Solid Films, vol. 425, nos. 1–2, pp. 255–259, 2003, doi: 10.1016/S0040-6090(02)01129-X.
  32. A. K. Sharma, A. K. Debnath, D. K. Aswal, and A. Mahajan, “Room-temperature ppb-level detection of chlorine using peripherally alkoxy-substituted phthalocyanine/SWCNTs-based chemiresistive sensors,” Sens. Actuators B Chem., vol. 350, Art. no. 130870, 2022, doi: 10.1016/j.snb.2021.130870.
  33. H. Karaca et al., “Metallophthalocyanines derived with phenyl sulfide by bridging triazole using click chemistry: Synthesis, computational study, redox chemistry and catalytic activity,” J. Mol. Struct., vol. 1236, Art. no. 130225, 2021, doi: 10.1016/j.molstruc.2021.130225.
  34. G. G. Çelik et al., “Influence of spacer and donor groups as tetraphenylethylene or triphenylamine in asymmetric zinc phthalocyanine dyes for dye-sensitized solar cells,” J. Photochem. Photobiol. A Chem., vol. 444, Art. no. 114962, 2023, doi: 10.1016/j.jphotochem.2023.114962.
  35. G. G. Köse, G. K. Karaoğlan, Y. E. Maden, and A. Koca, “Influence of 2-naphthoic acid anchoring groups on the photovoltaic performance of zinc phthalocyanine-based photosensitizers in dye-sensitized solar cells,” J. Electroanal. Chem., vol. 945, Art. no. 117691, 2023, doi: 10.1016/j.jelechem.2023.117691.
  36. A. C. Yüzer et al., “Solution-processed small-molecule organic solar cells based on non-aggregated zinc phthalocyanine derivatives: A comparative experimental and theoretical study,” Mater. Sci. Semicond. Process., vol. 129, Art. no. 105777, 2021, doi: 10.1016/j.mssp.2021.105777.
  37. H. Karaca, B. Çayeğil, and S. Sezer, “Synthesis, characterization and metal-sensing applications of novel chalcone-substituted phthalocyanines,” Synth. Met., vol. 215, pp. 134–141, 2016, doi: 10.1016/j.synthmet.2016.02.007.
  38. H. Karaca, “Redox chemistry, spectroelectrochemistry and catalytic activity of novel synthesized phthalocyanines bearing four Schiff bases on the periphery,” J. Organomet. Chem., vol. 822, pp. 39–45, 2016, doi: 10.1016/j.jorganchem.2016.08.013.
  39. H. Karaca, S. Sezer, and C. Tanyeli, “Synthesis of L-prolinol-substituted novel optically active phthalocyanines,” Dyes Pigments, vol. 90, no. 2, pp. 100–105, 2011, doi: 10.1016/j.dyepig.2010.12.003.
  40. M. Kınalı et al., “Chalcone-based dipolar cycloaddition of novel heteroaromatic compounds: Their anticancer examination,” J. Mol. Struct., vol. 1293, Art. no. 136244, 2023, doi: 10.1016/j.molstruc.2023.136244.
  41. H. V. Chavan, S. D. Ganapure, N. N. Mali, and P. S. Bhale, “Synthesis, characterization and biological evaluation of N-substituted indolyl chalcones as anticancer, anti-inflammatory and antioxidant agents,” Mater. Today Proc., vol. 73, pt. 3, pp. 396–402, 2023, doi: 10.1016/j.matpr.2022.09.264.
  42. I. F. de Farias et al., “Synthesis, characterization and molecular docking study of pyrazolines synthesized from chalcones: Antioxidant and acetylcholinesterase activities,” J. Mol. Struct., vol. 1291, Art. no. 135961, 2023, doi: 10.1016/j.molstruc.2023.135961.
  43. A. Suyambulingam, S. Nair, and K. Chellapandian, “Synthesis, spectral characterization of novel chalcones based oxazines derivatives and screening of their antimicrobial and antioxidant activity,” J. Mol. Struct., vol. 1268, Art. no. 133708, 2022, doi: 10.1016/j.molstruc.2022.133708.
  44. A. Siddiqa et al., “Synthesis, molecular docking, bio-evaluation and quantitative structure activity relationship of new chalcone derivatives as antioxidants,” J. Mol. Struct., vol. 1277, Art. no. 134814, 2023, doi: 10.1016/j.molstruc.2022.134814.
  45. M. Yadav, K. Lal, A. Kumar, P. Singh, V. K. Vishvakarma, and R. Chandra, “Click reaction inspired synthesis, antimicrobial evaluation and in silico docking of some pyrrole-chalcone linked 1,2,3-triazole hybrids,” J. Mol. Struct., vol. 1273, Art. no. 134321, 2023, doi: 10.1016/j.molstruc.2022.134321.
  46. J. Moreira et al., “New diarylpentanoids and chalcones as potential antimicrobial adjuvants,” Bioorg. Med. Chem. Lett., vol. 67, Art. no. 128743, 2022, doi: 10.1016/j.bmcl.2022.128743.
  47. T. N. M. Musthafa, K. Snigdha, A. M. Asiri, T. R. Sobahi, and M. Asad, “Green synthesis of chromonyl chalcone and pyrazoline as potential antimicrobial agents—DFT, molecular docking and antimicrobial studies,” J. Mol. Struct., vol. 1271, Art. no. 133993, 2023, doi: 10.1016/j.molstruc.2022.133993.
  48. S. Burmaoglu, E. A. Kazancioglu, M. Z. Kazancioglu, M. A. Alagoz, A. Dogen, and O. Algul, “Synthesis, in vitro biological evaluation, and molecular docking studies of novel biphenyl chalcone derivatives as antimicrobial agents,” Polycycl. Aromat. Compd., vol. 42, no. 9, pp. 5948–5961, 2022, doi: 10.1080/10406638.2021.1962925.
  49. D. Ušjak, B. Ivković, D. D. Božić, L. Bošković, and M. Milenković, “Antimicrobial activity of novel chalcones and modulation of virulence factors in hospital strains of Acinetobacter baumannii and Pseudomonas aeruginosa,” Microb. Pathog., vol. 131, pp. 186–196, 2019, doi: 10.1016/j.micpath.2019.04.015.
  50. X. Xu et al., “Synthesis, in vitro cytotoxicity evaluation and mechanism of 5′-monosubstituted chalcone derivatives as antitumor agents,” Bioorg. Med. Chem. Lett., vol. 85, Art. no. 129239, 2023, doi: 10.1016/j.bmcl.2023.129239.
  51. M. M. Amin et al., “Design, synthesis, cytotoxic activities, and molecular docking of chalcone hybrids bearing 8-hydroxyquinoline moiety with dual tubulin/EGFR kinase inhibition,” Bioorg. Chem., vol. 134, Art. no. 106444, 2023, doi: 10.1016/j.bioorg.2023.106444.
  52. A. Beytur et al., “Hexa-substituted cyclotriphosphazene derivatives containing hetero-ring chalcones: Synthesis, in vitro cytotoxic activity and their DNA damage determination,” Bioorg. Chem., vol. 127, Art. no. 105997, 2022, doi: 10.1016/j.bioorg.2022.105997.
  53. S. Koldas, I. Demirtas, D. Mutlu, M. N. Atalar, H. Ünver, and Ş. Arslan, “New cytotoxic chalcone derivatives from Astragalus ponticus Pall.,” Nat. Prod. Res., vol. 36, no. 18, pp. 4672–4680, 2022, doi: 10.1080/14786419.2021.2012771.
  54. L. Devi, G. Sharma, R. Kant, S. K. Shukla, and N. Rastogi, “Regioselective synthesis of functionalized pyrazole-chalcones via a base-mediated reaction of diazo compounds with pyrylium salts,” Org. Biomol. Chem., vol. 19, no. 18, pp. 4132–4136, 2021, doi: 10.1039/D1OB00274K.
  55. S. Farooq and Z. Ngaini, “One-pot and two-pot methods for chalcone-derived pyrimidines synthesis and applications,” J. Heterocycl. Chem., vol. 58, no. 6, pp. 1209–1224, 2021, doi: 10.1002/jhet.4226.
  56. N. Deshmukh and A. Shinde, “An efficient, ultrasound-induced ring closure of hydroxy chalcone in 2-ethoxy ethanol as an green reaction medium and study of antimicrobial potential,” Chem. Data Collect., vol. 31, Art. no. 100606, 2021, doi: 10.1016/j.cdc.2020.100606.
  57. C. F. S. Guazelli et al., “Antioxidant and anti-inflammatory effects of hesperidin methyl chalcone in experimental ulcerative colitis,” Chem.-Biol. Interact., vol. 333, Art. no. 109315, 2021, doi: 10.1016/j.cbi.2020.109315.
  58. S. C. Carr, M. A. Torres, J. S. Morris, P. J. Facchini, and K. K. S. Ng, “Structural studies of codeinone reductase reveal novel insights into aldo-keto reductase function in benzylisoquinoline alkaloid biosynthesis,” J. Biol. Chem., vol. 297, no. 4, Art. no. 101211, 2021, doi: 10.1016/j.jbc.2021.101211.
  59. H. L. Qin, Z. W. Zhang, L. Ravindar, and K. P. Rakesh, “Antibacterial activities with the structure–activity relationship of coumarin derivatives,” Eur. J. Med. Chem., vol. 207, Art. no. 112832, 2020, doi: 10.1016/j.ejmech.2020.112832.
  60. D. Das, “Lemon juice-mediated efficient and eco-friendly organic transformations,” Tetrahedron Lett., vol. 61, no. 36, Art. no. 152298, 2020, doi: 10.1016/j.tetlet.2020.152298.
  61. K. Trush and P. Paľove-Balang, “Biosynthesis and role of isoflavonoids in legumes under different environmental conditions,” Plant Stress, vol. 8, Art. no. 100153, Jun. 2023, doi: 10.1016/j.stress.2023.100153.
  62. J. Ma, J. Zhang, and Z. Shen, “Two unusual isoflavonoids from Campylotropis hirtella—A new biosynthesis route of flavonoids,” Tetrahedron Lett., vol. 58, no. 15, pp. 1462–1466, 2017, doi: 10.1016/j.tetlet.2017.02.080.
  63. A. Murugesan, R. M. Gengan, R. Rajamanikandan, M. Ilanchelian, and C.-H. Lin, “One-pot synthesis of Claisen–Schmidt reaction through (E)-chalcone derivatives: Spectral studies in human serum albumin protein binding and molecular docking investigation,” Synth. Commun., vol. 47, no. 20, pp. 1884–1904, 2017, doi: 10.1080/00397911.2017.1355466.
  64. A. Murugesan, R. M. Gengan, and C.-H. Lin, “Efficient synthesis of ethyl-piperazinyl quinolinyl-(E)-chalcone derivatives via Claisen–Schmidt reaction by using TiO₂-BPTETSA catalyst,” J. Taiwan Inst. Chem. Eng., vol. 80, pp. 852–866, 2017, doi: 10.1016/j.jtice.2017.07.014.
  65. M. N. Arshad et al., “Synthesis, crystal structures, spectroscopic and nonlinear optical properties of chalcone derivatives: A combined experimental and theoretical study,” J. Mol. Struct., vol. 1141, pp. 142–156, 2017, doi: 10.1016/j.molstruc.2017.03.090.
  66. D. Ergüntürk, M. B. Gürdere, Y. Budak, and M. Ceylan, “Synthesis, characterization, and investigations of antimicrobial activity of 6,6-dimethyl-3-aryl-3′,4′,6,7-tetrahydro-1′H,3H-spiro[benzofuran-2,2′-naphthalene]-1′,4(5H)-dione,” Synth. Commun., vol. 47, no. 16, pp. 1501–1506, 2017, doi: 10.1080/00397911.2017.1334918.
  67. N. Ndebele and T. Nyokong, “Electrocatalytic behaviour of chalcone-substituted Co, Cu, Mn and Ni phthalocyanines towards the detection of nitrite,” J. Electroanal. Chem., vol. 926, Art. no. 116951, Dec. 2022, doi: 10.1016/j.jelechem.2022.116951.
  68. G. Sarkı, H. Kantekin, H. Yalazan, N. Kahriman, Z. Bıyıklıoğlu, and V. Serdaroğlu, “Synthesis, characterization and electrochemical studies of metal-free and metallophthalocyanines containing two different chalcone units substituted on peripheral positions,” J. Mol. Struct., vol. 1196, pp. 592–603, 2019, doi: 10.1016/j.molstruc.2019.05.123.
  69. Y. I. Openda, B. Babu, and T. Nyokong, “Novel cationic-chalcone phthalocyanines for photodynamic therapy eradication of S. aureus and E. coli bacterial biofilms and MCF-7 breast cancer,” Photodiagn. Photodyn. Ther., vol. 38, Art. no. 102863, Jun. 2022, doi: 10.1016/j.pdpdt.2022.102863.
  70. T. Arslan, “Design and synthesis of novel peripherally tetra-chalcone-substituted phthalocyanines and their inhibitory effects on acetylcholinesterase and carbonic anhydrases (hCA I and II),” J. Organomet. Chem., vol. 951, Art. no. 122021, 2021, doi: 10.1016/j.jorganchem.2021.122021.
  71. X. F. Zhang, Y. Lin, W. Guo, and J. Zhu, “Spectroscopic insights on imidazole-substituted phthalocyanine photosensitizers: Fluorescence properties, triplet state and singlet oxygen generation,” Spectrochim. Acta A Mol. Biomol. Spectrosc., vol. 133, pp. 752–758, 2014, doi: 10.1016/j.saa.2014.06.063.
  72. H. Karaca and S. Kazancı, “The metal sensing applications of chalcones: The synthesis, characterization and theoretical calculations,” J. Mol. Struct., vol. 1248, Art. no. 131454, Jan. 2022, doi: 10.1016/j.molstruc.2021.131454.
  73. A. Baran, S. Çol, E. Karakılıç, and F. Özen, “Photophysical, photochemical and DNA binding studies of prepared phthalocyanines,” Polyhedron, vol. 175, Art. no. 114205, 2020, doi: 10.1016/j.poly.2019.114205.
  74. H. Shinohara, O. Tsaryova, G. Schnurpfeil, and D. Wöhrle, “Differently substituted phthalocyanines: Comparison of calculated energy levels, singlet oxygen quantum yields, photo-oxidative stabilities, photocatalytic and catalytic activities,” J. Photochem. Photobiol. A Chem., vol. 184, no. 1, pp. 50–57, 2006, doi: 10.1016/j.jphotochem.2006.03.024.
  75. Y. Pan, W. Chen, S. Lu, and Y. Zhang, “Novel aqueous-soluble cobalt phthalocyanine: Synthesis and catalytic activity on oxidation of 2-mercaptoethanol,” Dyes Pigments, vol. 66, no. 2, pp. 115–121, 2005, doi: 10.1016/j.dyepig.2004.09.018.
  76. V. I. Iliev, A. I. Ileva, and L. D. Dimitrov, “Catalytic oxidation of 2-mercaptoethanol by cobalt(II)-phthalocyanine complexes intercalated in layered double hydroxides,” Appl. Catal. A Gen., vol. 126, no. 2, pp. 333–340, 1995, doi: 10.1016/0926-860X(95)00027-5.
  77. W. Chidawanyika and T. Nyokong, “Spectroscopic and photophysicochemical behaviour of novel cadmium phthalocyanine derivatives tetra-substituted at the alpha and beta positions,” J. Photochem. Photobiol. A Chem., vol. 202, nos. 2–3, pp. 99–106, 2009, doi: 10.1016/j.jphotochem.2008.11.014.
  78. M. J. Frisch et al., Gaussian 16, Revision C.01. Wallingford, CT, USA: Gaussian, Inc., 2016.
  79. R. Dennington, T. A. Keith, and J. M. Millam, GaussView, ver. 6. Shawnee Mission, KS, USA: Semichem Inc., 2016.
  80. C. Lee, W. Yang, and R. G. Parr, “Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density,” Phys. Rev. B, vol. 37, no. 2, pp. 785–789, Jan. 1988, doi: 10.1103/PhysRevB.37.785.
  81. M. S. Ağırtaş, C. Karataş, and S. Özdemir, “Synthesis of some metallophthalocyanines with dimethyl 5-(phenoxy)-isophthalate substituents and evaluation of their antioxidant-antibacterial activities,” Spectrochim. Acta A Mol. Biomol. Spectrosc., vol. 135, pp. 20–24, 2015, doi: 10.1016/j.saa.2014.06.139.
  82. M. S. Ağırtaş and M. S. İzgi, “Synthesis and characterization of new metallophthalocyanines with four phenoxyacetamide units,” J. Mol. Struct., vol. 927, nos. 1–3, pp. 126–128, 2009, doi: 10.1016/j.molstruc.2009.03.011.
  83. M. S. Ağırtaş, “Highly soluble phthalocyanines with hexadeca-tert-butyl substituents,” Dyes Pigments, vol. 79, no. 3, pp. 247–251, 2008, doi: 10.1016/j.dyepig.2008.03.004.
  84. M. S. Ağırtaş, “Non-aggregating phthalocyanines with bulky 2,4-di-tert-butylphenoxy substituents,” Dyes Pigments, vol. 74, no. 2, pp. 490–493, 2007, doi: 10.1016/j.dyepig.2006.03.009.
  85. P. R. Somani and S. Radhakrishnan, “Electrochromic materials and devices: Present and future,” Mater. Chem. Phys., vol. 77, no. 1, pp. 117–133, Jan. 2003, doi: 10.1016/S0254-0584(01)00575-2.
  86. N. Nombona and T. Nyokong, “The synthesis, cyclic voltammetry and spectroelectrochemical studies of Co(II) phthalocyanines tetra-substituted at the α and β positions with phenylthio groups,” Dyes Pigments, vol. 80, no. 1, pp. 130–135, 2009, doi: 10.1016/j.dyepig.2008.06.002.
  87. H. Karaca, “Catalytic oxidation of 2-mercaptoethanol by cobalt(II) phthalocyanines bearing chalcone with furan and thiophene,” Sakarya Univ. J. Sci., vol. 22, no. 6, pp. 1699–1703, Dec. 2018, doi: 10.16984/saufenbilder.407781.