{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,13]],"date-time":"2026-05-13T23:39:36Z","timestamp":1778715576911,"version":"3.51.4"},"reference-count":63,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2022,6,14]],"date-time":"2022-06-14T00:00:00Z","timestamp":1655164800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"King Khalid University","award":["R.G.P-1\/3\/43"],"award-info":[{"award-number":["R.G.P-1\/3\/43"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This study describes the synthesis, theoretical investigations, and photocatalytic degradational properties of a new (pyrazine)(meso-tetrakis(4-tert-methoxyphenyl)-porphyrinato)-cadmium (II) ([Cd(TMPP)-Pyz]) complex (1). The new penta-coordinated CdII porphyrin complex (1) was characterized by various spectroscopic techniques, including FT-IR, NMR, UV-visible absorption, fluorescence emission, and singlet oxygen, while its molecular structure was studied using single crystal X-ray diffraction. The UV\u2013Vis spectroscopic study highlighted the redshift of the absorption bands after the insertion of the Cd(II) metal ion into the TMPP ring. The co-coordination of the pyrazine axial ligand enhanced this effect. A fluorescence emission spectroscopic study showed a significant blueshift in the Q bands, accompanied by a decrease in the fluorescence emission intensity and quantum yields of \u03a6f = 0.084, \u03a6f = 0.06 and \u03a6f = 0.03 for H2-TMPP free-base porphyrin, [Cd(TMPP)] and [Cd(TMPP)(Pyz)] (1) respectively. Singlet oxygen revealed that the H2-TMPP porphyrin produced the most efficient singlet oxygen quantum yield of (\u03a6\u0394 = 0.73) compared to [CdTMPP] (\u03a6\u0394 = 0.57) and [Cd(TMPP)(Pyz)] (1) (\u03a6\u0394 = 0.13). In the crystal lattice, the [Cd(TMPP)Pyz] was stabilized through non-covalent intermolecular interactions (NCI), such as the hydrogen bonds C-H\u00b7\u00b7\u00b7N and C-H\u00b7\u00b7\u00b7Cg. Additionally, crystal explorer software was then utilized to measure the quantitative analysis of the intermolecular interactions in the unit cell of the crystal structure and established that the C-H\u00b7\u00b7\u00b7\u03c0 interaction dominated. The Natural bond orbital (NBO) analysis revealed that each molecule is stabilized by hyperconjugation and charge delocalization. As a photocatalyst, the coordination complex 1 showed excellent photocatalytic activity toward the degradation of Levafix Blue CA reactive dye (i.e., dye photo-degradation of 80%).<\/jats:p>","DOI":"10.3390\/molecules27123833","type":"journal-article","created":{"date-parts":[[2022,6,15]],"date-time":"2022-06-15T01:39:54Z","timestamp":1655257194000},"page":"3833","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Synthesis, Characterization, DFT and Photocatalytic Studies of a New Pyrazine Cadmium(II) Tetrakis(4-methoxy-phenyl)-porphyrin Compound"],"prefix":"10.3390","volume":"27","author":[{"given":"Chadlia","family":"Mchiri","sequence":"first","affiliation":[{"name":"Laboratoire de Physico-Chimie des Mat\u00e9riaux (LPCM), Facult\u00e9 des Sciences de Monastir, Avenue de l\u2019environnement, University of Monastir, Monastir 5019, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3003-3025","authenticated-orcid":false,"given":"Louis-Charl C.","family":"Coetzee","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of South Africa, Private Bag X6, Florida, Roodepoort, Johannesburg 1710, Gauteng, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2806-4343","authenticated-orcid":false,"given":"Faycal","family":"Chandoul","sequence":"additional","affiliation":[{"name":"Faculty of Mathematical, Physical and Natural Sciences of Tunis, University of Tunis El Manar, Tunis 2092, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4070-3299","authenticated-orcid":false,"given":"Abdesslem","family":"Jedidi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2318-8208","authenticated-orcid":false,"given":"Adedapo S.","family":"Adeyinka","sequence":"additional","affiliation":[{"name":"Research Centre for Synthesis and Catalysis, Department of Chemical Sciences, University of Johannesburg, Auckland Park, Johannesburg 2006, Gauteng, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nomampondo","family":"Magwa","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of South Africa, Private Bag X6, Florida, Roodepoort, Johannesburg 1710, Gauteng, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6088-4472","authenticated-orcid":false,"given":"Thierry","family":"Roisnel","sequence":"additional","affiliation":[{"name":"Centre de Diffractom\u00e9trie X, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS\u2013Universit\u00e9 de Rennes 1, Campus de Beaulieu, 35042 Rennes, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sana","family":"Ben Moussa","sequence":"additional","affiliation":[{"name":"Faculty of Science and Arts, Mohail Asser, King Khalid University, Abha 61421, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Habib","family":"Nasri","sequence":"additional","affiliation":[{"name":"Laboratoire de Physico-Chimie des Mat\u00e9riaux (LPCM), Facult\u00e9 des Sciences de Monastir, Avenue de l\u2019environnement, University of Monastir, Monastir 5019, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,6,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"833","DOI":"10.1002\/pi.4908","article-title":"Porphyrin polymers and organic frameworks","volume":"64","author":"Day","year":"2015","journal-title":"Polym. Int."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1038","DOI":"10.1016\/j.chemosphere.2018.08.122","article-title":"Facile one-pot synthesis of a porphyrin based hydrophilic porous organic polymer and application as recyclable absorbent for selective separation of methylene blue","volume":"212","author":"Liu","year":"2018","journal-title":"Chemosphere"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"10534","DOI":"10.1007\/s10853-018-2305-5","article-title":"Synthesis and characterization of porphyrin-based porous coordination polymers obtained by supercritical CO2 extraction","volume":"53","author":"Xu","year":"2018","journal-title":"J. Mater. Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2618","DOI":"10.1002\/anie.201106203","article-title":"High-rate charge-carrier transport in porphyrin covalent organic frameworks","volume":"51","author":"Feng","year":"2012","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"2802","DOI":"10.1002\/cssc.201900139","article-title":"Solar cells sensitized with porphyrin dyes containing oligo (Ethylene Glycol) units: A high efficiency beyond 12%","volume":"12","author":"Lu","year":"2019","journal-title":"ChemSusChem"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4","DOI":"10.1021\/jacs.9b12675","article-title":"Efficient solar cells based on concerted companion dyes containing two complementary components: An alternative approach for cosensitization","volume":"142","author":"Zeng","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1127","DOI":"10.1039\/B919645E","article-title":"Synthesis and characterization of porphyrin sensitizers with various electron donating substituents for highly efficient dye sensitized solar cells","volume":"20","author":"Hsieh","year":"2010","journal-title":"J. Mater. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"109136","DOI":"10.1016\/j.dyepig.2021.109136","article-title":"Porphyrin-based compounds and their applications in materials and medicine","volume":"188","author":"Yingyan","year":"2021","journal-title":"Dye Pigment."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/j.dyepig.2018.07.045","article-title":"Synthesis of new TiO2\/porphyrin-based composites and photocatalytic studies on methylene blue degradation","volume":"160","author":"Min","year":"2019","journal-title":"Dye Pigment."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"491","DOI":"10.1021\/jp0747151","article-title":"Visible Light Photocatalysts Based on Homogeneous and Heterogenized Tin Porphyrins","volume":"112","author":"Kim","year":"2008","journal-title":"J. Phys. Chem. C"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"9606","DOI":"10.1021\/es301775k","article-title":"Selective oxidative degradation of organic pollutants by singlet oxygen mediated photosensitization: Tin porphyrin versus C60 Aminofullerene systems","volume":"46","author":"Kim","year":"2012","journal-title":"Environ. Sci. Technol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"784","DOI":"10.1016\/j.chemosphere.2015.08.007","article-title":"Toxic textile dyes accumulate in wild European eel Anguilla Anguilla","volume":"138","author":"Belpaire","year":"2015","journal-title":"Chemosphere"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.cej.2018.12.050","article-title":"Iron-modified composite adsorbent coating for azo dye removal and its regeneration by photo-Fenton process: Synthesis, characterization and adsorption mechanism interpretation","volume":"361","author":"Azha","year":"2019","journal-title":"Chem. Eng. J."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1039\/C8TA07109H","article-title":"Hypervalent silicon-based, anionic porous organic polymers with solid microsphere or hollow nanotube morphologies and exceptional capacity for selective adsorption of cationic dyes","volume":"7","author":"Xiong","year":"2019","journal-title":"J. Mater. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1255","DOI":"10.1039\/C8CS00882E","article-title":"Heterogeneous photocatalysts: An overview of classic and modern approaches for optical, electronic, and charge dynamics evaluation","volume":"48","author":"Tan","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3128","DOI":"10.1038\/s41598-017-03347-y","article-title":"Constructing a visible-light-driven photocatalytic membrane by g-C3N4 quantum dots and TiO2 nanotube array for enhanced water treatment","volume":"7","author":"Zhang","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"134","DOI":"10.1016\/j.molliq.2018.05.050","article-title":"Synthesis of the (4,4\u2032-bipyridine)(5,10,15,20-tetratolylphenylporphyrinato)-zinc(II) bis(4,4-bipyridine) disolvate dehydrate and Evaluation of its interaction with organic dyes","volume":"264","author":"Soury","year":"2018","journal-title":"J. Mol. Liq."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1021\/ic302273h","article-title":"Unprecedented (3,10)-Connected 2-D Metal\u2212Organic Framework Constructed from Octanuclear Cobalt(II) Clusters and a New Bifunctional Ligand","volume":"52","author":"Wen","year":"2013","journal-title":"J. Inorg. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"187","DOI":"10.11648\/j.ijnfs.20170605.11","article-title":"Toxic Effects of Levafix Blue CA and Levafix Amber CA Reactive Dyes on Liver and Kidney in Mice","volume":"6","author":"Rahman","year":"2017","journal-title":"Int. J. Food Sci. Nutr."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1016\/j.jhazmat.2007.06.010","article-title":"Electrochemical treatment of simulated textile wastewater with industrial components and Levafix Blue CA reactive dye: Optimization through response surface methodology","volume":"151","author":"Korbahti","year":"2008","journal-title":"J. Hazard. Mater."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"120046","DOI":"10.1016\/j.ica.2020.120046","article-title":"DABCO Cadmium(II) Tetrakis(4-methoxyphenyl)porphyrin Complex\u2013Structure, Photophysical properties, and Adsorpion removal of methylene blue dye","volume":"515","author":"Mchiri","year":"2020","journal-title":"Inorg. Chim. Acta"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"114107","DOI":"10.1016\/j.poly.2019.114107","article-title":"Distorted five-coordinate square pyramidal geometry of a cadmium(II) complex containing a 2-methylimidazole ligand: Crystal structure and axial ligand effect on spectroscopic properties","volume":"173","author":"Mchiri","year":"2019","journal-title":"Polyhedron"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1233","DOI":"10.1016\/j.inoche.2004.09.015","article-title":"Cadmium complexes of meso-tetra-(p-chlorophenyl)-porphyrin: [meso-tetra-(p-chlorophenyl)-porphyrinato](pyridine)cadmium(II) pyridine solvate and [meso-tetra-(p-chlorophenyl)porphyrinato]-(dimethylformamide)cadmium(II) toluene solvate","volume":"7","author":"Wun","year":"2004","journal-title":"Inorg. Chem. Commun."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"6549","DOI":"10.1021\/ja00017a028","article-title":"Porphyrin Sponges. Structural Systematics of the Host Lattice","volume":"113","author":"Byrn","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1053","DOI":"10.5012\/bkcs.2006.27.7.1053","article-title":"Synthesis, characterization and crystal structure of (\u03b1- aminopyridine-N)-(5,10,15,20-tetraphenylporphyrinato) cadmium(II) acetone solvate","volume":"27","author":"Zhao","year":"2006","journal-title":"Bull. Korean Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1557","DOI":"10.1107\/S1600536812048052","article-title":"Di-\u03bc-azido-bis-(\u03bc-1,4,7,10,13,16-hexa-oxacyclo-octa-deca-ne)bis-(5,10,15,20-tetra-phenyl-porphyrinato)dicadmium-disodium","volume":"68","author":"Toumi","year":"2012","journal-title":"Acta Crystallogr. Sect. E Struct. Rep. Online"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/BFb0036789","article-title":"Recent advances in the stereochemistry of metallotetrapyrroles","volume":"64","author":"Scheidt","year":"1987","journal-title":"Struct. Bond."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4733","DOI":"10.1021\/j100268a017","article-title":"Substituent effects on the electronic structure of metalloporphyrins: A quantitative analysis in terms of four-orbital-model parameters","volume":"89","author":"Shelnutt","year":"1985","journal-title":"J. Phys. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5500","DOI":"10.1039\/C5NJ00014A","article-title":"Synthesis of 2-nitro-3-(pyrrol-1-yl)-5,10,15,20-tetraarylporphyrins via a Clauson-Kaas reaction and the study of their electronic properties","volume":"39","author":"Tiwari","year":"2015","journal-title":"New J. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"6352","DOI":"10.1039\/D1RA09346K","article-title":"Synthesis, spectroscopic findings and crystal engineering of Pb(II)-Salen coordination polymers, and supramolecular architectures engineered by \u03c3-hole\/spodium\/tetral bonds: A combined experimental and theoretical investigation","volume":"12","author":"Majumdar","year":"2022","journal-title":"RSC. Adv."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/j.microc.2012.07.002","article-title":"Application of the electronic spectra of porphyrins for analytical purposes: The effects of metal ions and structural distortions","volume":"107","author":"Valicsek","year":"2013","journal-title":"Microchem. J."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"627","DOI":"10.1002\/pssb.19660150224","article-title":"Optical Properties and Electronic Structure of Amorphous Germanium","volume":"15","author":"Tauc","year":"1966","journal-title":"Phys. Status Solidi B"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"5824","DOI":"10.1021\/jp801395h","article-title":"Photophysics of Soret-excited Tetrapyrroles in solution. I. Metalloporphyrins: MgTPP, ZnTPP, and CdTPP","volume":"112","author":"Tripathy","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1","DOI":"10.2174\/1874383801105010001","article-title":"Substituent Effects of Porphyrin on Singlet Oxygen Generation Quantum Yields","volume":"5","author":"Nifiatis","year":"2011","journal-title":"Open. Spectros. J."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1142\/S1088424602000026","article-title":"Bis(aryloxo) derivatives of tin (IV) porphyrins: Synthesis, spectroscopy and redox activity","volume":"6","author":"Reddy","year":"2002","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.poly.2019.06.055","article-title":"Insights into the New Cadmium(II) Metalloporphyrin: Synthesis, X-ray Crystal Structure, Hirshfeld surface analysis, Photophysical and Cyclic voltammetry Characterization of the (Morpholine){(meso-tetra(parachloro-phenyl)porphyrinato}cadmium(II)","volume":"171","author":"Mchiri","year":"2019","journal-title":"Polyhedron"},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Chen, Y., Li, A., Huang, Z.H., Wang, L.N., and Kang, F. (2016). Porphyrin-Based Nanostructures for Photocatalytic Applications. Nanomaterials, 6.","DOI":"10.3390\/nano6030051"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4077","DOI":"10.1021\/ja00011a004","article-title":"Relationships between Structural Parameters and Raman Frequencies for Some Planar and Nonplanar Nickel(II) Porphyrins","volume":"113","author":"Shelnutt","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"104340","DOI":"10.1016\/j.reactfunctpolym.2019.104340","article-title":"A 1D porphyrin-based rigid conjugated polymer as efficient and recyclable visible-light driven photocatalyst","volume":"143","author":"Yua","year":"2019","journal-title":"React. Funct. Polym."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"109774","DOI":"10.1016\/j.micromeso.2019.109774","article-title":"Porphyrin-based porous organic polymer, Py-POP, as a multifunctional platform for efficient selective adsorption and photocatalytic degradation of cationic dyes","volume":"292","author":"Li","year":"2020","journal-title":"Microporous Mesoporous Mater."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"20763","DOI":"10.1021\/jacs.0c09727","article-title":"Photocatalytic Molecular Oxygen Activation by Regulating Excitonic Effects in Covalent Organic Frameworks","volume":"142","author":"Li","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/0022-2852(69)90335-X","article-title":"Fluorescence Spectra and Quantum Yields","volume":"31","author":"Seybold","year":"1969","journal-title":"J. Mol. Spectrosc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1111\/j.1751-1097.1999.tb08240.x","article-title":"A compilation of singlet oxygen yields from biologically relevant molecules","volume":"70","author":"Redmond","year":"1999","journal-title":"Photochem. Photobiol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1107\/S0567739474000337","article-title":"Extinction within the Limit of Validity of the Darwin Transfer Equations. I. General Formalisms for Primary and Secondary Extinction and Their Application to Spherical Crystals","volume":"A30","author":"Becker","year":"1974","journal-title":"Acta Crystallogr."},{"key":"ref_45","first-page":"435","article-title":"SIRPOW.92\u2014A program for automatic solution of crystal structures by direct methods optimized for powder data","volume":"27","author":"Altomare","year":"1994","journal-title":"J. Appl. Crystallogr."},{"key":"ref_46","first-page":"3","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."},{"key":"ref_47","first-page":"9","article-title":"PLATON SQUEEZE: A tool for the calculation of the disordered solvent contribution to the calculated structure factors","volume":"C71","author":"Spek","year":"2015","journal-title":"Acta Cryst."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1107\/S0021889807067908","article-title":"Wood, Mercury CSD 2.0\u2014New Features for the Visualization and Investigation of Crystal Structures","volume":"41","author":"Macrae","year":"2008","journal-title":"J. Appl. Cryst."},{"key":"ref_49","unstructured":"Frisch, G.M., Trucks, J.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Salman, G., Barone, V., Mennucci, B., and Petersson, G.A. (2009). Gaussian 09, Gaussian Inc.. Revision A.02."},{"key":"ref_50","unstructured":"Dennington, R.R., Keith, T., and Millam, J. (2009). GaussView, Semichem Inc.. Version 5."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"11623","DOI":"10.1021\/j100096a001","article-title":"Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields","volume":"98","author":"Stephens","year":"1994","journal-title":"J. Phys. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"9342","DOI":"10.1021\/ja0630285","article-title":"Popular theoretical methods predict benzene and arenes to be nonplanar","volume":"128","author":"Simmonett","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1730","DOI":"10.1063\/1.456066","article-title":"Energy-adjusted ab initio pseudopotentials for the rare earth elements","volume":"90","author":"Dolg","year":"1989","journal-title":"J. Chem. Phys."},{"key":"ref_54","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_55","doi-asserted-by":"crossref","unstructured":"Jiao, Y., and Weinhold, F. (2019). What Is the Nature of Supramolecular Bonding Comprehensive NBO\/NRT Picture of Halogen and Pnicogen Bonding in RPH2\u00b7IF\/FI Complexes (R = CH3, OH, CF3, CN, NO2). Molecules, 24.","DOI":"10.3390\/molecules24112090"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Jiao, Y., and Weinhold, F. (2020). NBO\/NRT Two-State Theory of Bond-Shift Spectral Excitation. Molecules, 25.","DOI":"10.3390\/molecules25184052"},{"key":"ref_57","unstructured":"Glendenning, E.D., Reed, A.E., Carpenter, J.E., and Weinhold, F. (2001). NBO, Version 3.1, Gaussian Inc."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","article-title":"CrystalExplorer: A program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"ref_59","first-page":"175","article-title":"Microwave-assisted synthesis of 5,10,15,20-tetrakis(4-nitrophenyl) porphyrin and zinc derivative and study of their bacterial photoinactivation","volume":"4","author":"Rahimia","year":"2016","journal-title":"Iran. Chem. Commun."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1002\/jhet.78","article-title":"Microwave-Assisted Synthesis, Metallation, and Duff Formylation of Porphyrins","volume":"46","author":"Yaseen","year":"2009","journal-title":"J. Heterocyclic Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1562\/0031-8655(2001)074<0014:PSOMTM>2.0.CO;2","article-title":"Photodynamic Studies of Metallo 5,10,15,20-Tetrakis(4-methoxyphenyl) porphyrin: Photochemical Characterization and Biological Consequences in a Human Carcinoma Cell Line","volume":"74","author":"Alvarez","year":"2001","journal-title":"Photochem. Photobiol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1233","DOI":"10.1016\/j.inoche.2004.09.015","article-title":"Cadmium complexes of meso-tetra-(p-chlorophenyl) porphyrin:[meso-tetra-(p-chlorophenyl)porphyrinato](pyridine)cadmium(II)pyridine solvate and [meso-tetra-(p-chlorophenyl)porphyrinato](dimethylformamide)cadmium(II) toluene solvate","volume":"7","author":"Wun","year":"2004","journal-title":"Inorg. Chem. Commun."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1016\/0009-2614(95)01030-D","article-title":"Unusual picosecond 1 (\u03c0, \u03c0 *) deactivation of ruffled nonplanar porphyrins","volume":"245","author":"Gentemann","year":"1995","journal-title":"Chem. Phys. Lett."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/12\/3833\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:31:27Z","timestamp":1760139087000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/12\/3833"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,6,14]]},"references-count":63,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2022,6]]}},"alternative-id":["molecules27123833"],"URL":"https:\/\/doi.org\/10.3390\/molecules27123833","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,6,14]]}}}