{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,27]],"date-time":"2026-07-27T14:56:29Z","timestamp":1785164189708,"version":"3.55.0"},"reference-count":33,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2025,6,22]],"date-time":"2025-06-22T00:00:00Z","timestamp":1750550400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This study introduces a newly synthesized Co(II) phthalocyanine complex (Co-Pc, 4) incorporating two (mercapto-terphenyl)thio-dione substituents, along with a detailed exploration of its structural, spectroscopic, and binding characteristics. The key precursor, 4-[(4\u2032\u2032-mercapto-[1,1\u2032:4\u2032,1\u2032\u2032-terphenyl]-4-yl)thio]phthalonitrile (compound 3), was first obtained and subsequently used to construct the phthalocyanine macrocycle through cyclotetramerization in the presence of cobalt and zinc salts under heat and vacuum in dimethylformamide. The resulting compounds (3 and 4) were characterized using a comprehensive array of analytical techniques, including elemental analysis, UV\u2013Vis spectroscopy, FT-IR, 1H-NMR, and Q-TOF mass spectrometry. Additionally, density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were employed to elucidate the electronic structure and geometrical features of Co-Pc 4, providing theoretical support for the experimental findings. The integration of theoretical and experimental findings provides in-depth insight into the electronic behavior and reactivity of compound 4, highlighting its promise as a candidate for photovoltaic applications. Further studies may investigate how structural modifications influence these properties, potentially leading to improved device performance.<\/jats:p>","DOI":"10.3390\/molecules30132693","type":"journal-article","created":{"date-parts":[[2025,6,23]],"date-time":"2025-06-23T04:50:05Z","timestamp":1750654205000},"page":"2693","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Structure\u2013Function Relationship of Novel Tetrakis (Mercapto-Terphenyl)Benzene Cobalt (II) Phthalocyanines: Synthesis and Computational Evaluation"],"prefix":"10.3390","volume":"30","author":[{"given":"Sevil","family":"Sener","sequence":"first","affiliation":[{"name":"Department of Chemical Technology Program, Aliaga Vocational School, Ege University, Izmir 35040, T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nursel","family":"Acar-Selcuki","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Ege University, Izmir 35100, T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,6,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1585","DOI":"10.1039\/b701257h","article-title":"2,6-Diaryl-9,10-Anthraquinones as Models for Electron-Accepting Polymers","volume":"31","author":"Gautrot","year":"2007","journal-title":"New J. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1070\/MC2002v012n03ABEH001573","article-title":"Preparation of 1,2-Bis(3,4-Dicyanophenoxymethyl)Benzene and the Binuclear Zinc Phthalocyanine Derived from It","volume":"12","author":"Tolbin","year":"2002","journal-title":"Mendeleev Commun."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"127653","DOI":"10.1016\/j.molstruc.2019.127653","article-title":"New Square-Planar Nickel(II)-Triphenylphosphine Complexes Containing ONS Donor Ligands: Synthesis, Characterization, Electrochemical and Antioxidant Properties","volume":"1206","author":"Kaya","year":"2020","journal-title":"J. Mol. Struct."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3570","DOI":"10.1021\/cm990138k","article-title":"Synthesis of Saturated and Unsaturated Curtis-Type Ni Derivatives as 2,6-Dihydroxyanthraquinonates. Crystal and Molecular Structure. Thin Film Measurements of Conductivity and Ab Initio Calculations of Electronic States","volume":"12","author":"Cogordan","year":"2000","journal-title":"Chem. Mater."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"11179","DOI":"10.1039\/C6TA03123D","article-title":"Quinone and Its Derivatives for Energy Harvesting and Storage Materials","volume":"4","author":"Son","year":"2016","journal-title":"J. Mater. Chem. A"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1016\/j.ccr.2014.02.003","article-title":"The Coordination Chemistry of Substituted Anthraquinones: Developments and Applications","volume":"269","author":"Pope","year":"2014","journal-title":"Coord. Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"774","DOI":"10.1016\/j.ejmech.2017.07.009","article-title":"Azaphenothiazines\u2014Promising Phenothiazine Derivatives. An Insight into Nomenclature, Synthesis, Structure Elucidation and Biological Properties","volume":"138","author":"Pluta","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"682","DOI":"10.1016\/j.msec.2005.06.028","article-title":"Computer Simulation of Electron Transfer in Molecular Electronic Devices","volume":"25","author":"Correia","year":"2005","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/j.nanoen.2016.12.015","article-title":"Thiol-Based Electrolyte Additives for High-Performance Lithium-Sulfur Batteries","volume":"32","author":"Wu","year":"2017","journal-title":"Nano Energy"},{"key":"ref_10","unstructured":"Farrugia, V.M., Birau, M.M., Iftime, G., and Abraham, B.E. (2015). Alizarin-Based Polymer Colorants. (9181389B2), US."},{"key":"ref_11","unstructured":"Shimizu, T., Kaneko, I., and Watanabe, M. (1991). Method of Preventing Polymer-Scale Formation. (4,933,399), US Patent."},{"key":"ref_12","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (G16_C01 2016, 2016). G16_C01 2016, Gaussian 16, Revision C.01."},{"key":"ref_13","unstructured":"Dennington, R., Keith, T.A., and Millam, J.M. (GaussView, 2016). GaussView, version 6.0.16."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1186\/1758-2946-4-17","article-title":"Avogadro: An Advanced Semantic Chemical Editor, Visualization, and Analysis Platform","volume":"4","author":"Hanwell","year":"2012","journal-title":"J. Cheminform."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"B864","DOI":"10.1103\/PhysRev.136.B864","article-title":"Inhomogeneous Electron Gas","volume":"136","author":"Hohenberg","year":"1964","journal-title":"Phys. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"A1133","DOI":"10.1103\/PhysRev.140.A1133","article-title":"Self-Consistent Equations Including Exchange and Correlation Effects","volume":"140","author":"Kohn","year":"1965","journal-title":"Phys. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"154104","DOI":"10.1063\/1.3382344","article-title":"A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu","volume":"132","author":"Grimme","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density-Functional Thermochemistry. III. The Role of Exact Exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1016\/S0065-3276(08)60600-0","article-title":"Time-Dependent Density-Functional Theory","volume":"Volume 21","year":"1990","journal-title":"Density Functional Theory of Many-Fermion Systems"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2193","DOI":"10.1063\/1.455064","article-title":"A Complete Basis Set Model Chemistry. I. The Total Energies of Closed-shell Atoms and Hydrides of the First-row Elements","volume":"89","author":"Petersson","year":"1988","journal-title":"J. Chem. Phys."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/S0166-1280(98)00553-3","article-title":"The IEF Version of the PCM Solvation Method: An Overview of a New Method Addressed to Study Molecular Solutes at the QM Ab Initio Level","volume":"464","author":"Tomasi","year":"1999","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/cr9904009","article-title":"Quantum Mechanical Continuum Solvation Models","volume":"105","author":"Tomasi","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1081\/SIM-200052678","article-title":"Complexes of Ag(I), TI(I), Zn(II), Hg(II), Cd(II), Pd(II), Co(II) and Ni(II) with 4-[(4-Dimethylamino-benzylidene)-amino]-5-ethyl-2,4-dihydro-[1,2,4]Triazole-3-thione (HDEDT) and 4-[(Benzylidene)Amino]-6-(T-butyl)-4H-[1,2,4]-triazine-3-thione-5-one (HBBTT)","volume":"35","author":"Bhat","year":"2005","journal-title":"Synth. React. Inorg. Met.-Org. Nano-Met. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1002\/jctb.280450306","article-title":"Marine Coatings Based on Metal Complexes of 4-Amino-3-Hydrazino-5-Thio-1,2,4-Triazole","volume":"45","author":"Tadros","year":"1989","journal-title":"J. Chem. Technol. Biotechnol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"116738","DOI":"10.1016\/j.poly.2023.116738","article-title":"Electrical, Spectroscopic and DFT Studies of Synthesized Bridged Bis (2-Oxy Benzylidene) Hydrazine-Carbonothioly-Hydrazono Cobalt(II)Phthalocyanine","volume":"247","author":"Sener","year":"2024","journal-title":"Polyhedron"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"124","DOI":"10.1016\/j.ejps.2018.12.017","article-title":"Synthesis, Characterization, and DFT Study of Novel Metallo Phtalocyanines with Four Carboranyl Clusters as Photosensitisers for the Photodynamic Therapy of Breast Cancer Cells","volume":"129","author":"Tozlu","year":"2019","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"122614","DOI":"10.1016\/j.ica.2025.122614","article-title":"Synthesized Tetrakis (2-Oxy Benzylidene)\u2014Hyroanthracen-2-Yloxy Zinc and Cobalt (II) Phthalocyanines: Structural, DFT and SEM-EDS Study","volume":"581","author":"Cavdan","year":"2025","journal-title":"Inorganica Chim. Acta"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/0025-5408(68)90023-8","article-title":"Optical Properties and Electronic Structure of Amorphous Ge and Si","volume":"3","author":"Tauc","year":"1968","journal-title":"Mater. Res. Bull."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A Multifunctional Wavefunction Analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"082503","DOI":"10.1063\/5.0216272","article-title":"A Comprehensive Electron Wavefunction Analysis Toolbox for Chemists, Multiwfn","volume":"161","author":"Lu","year":"2024","journal-title":"J. Chem. Phys."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"6498","DOI":"10.1021\/ja100936w","article-title":"Revealing Noncovalent Interactions","volume":"132","author":"Johnson","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1126\/science.218.4574.747","article-title":"Role of Frontier Orbitals in Chemical Reactions","volume":"218","author":"Fukui","year":"1982","journal-title":"Science"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/13\/2693\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T17:56:29Z","timestamp":1760032589000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/13\/2693"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,6,22]]},"references-count":33,"journal-issue":{"issue":"13","published-online":{"date-parts":[[2025,7]]}},"alternative-id":["molecules30132693"],"URL":"https:\/\/doi.org\/10.3390\/molecules30132693","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,6,22]]}}}