{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T19:16:06Z","timestamp":1788290166748,"version":"build-2803163510"},"reference-count":145,"publisher":"American Chemical Society (ACS)","issue":"34","license":[{"start":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T00:00:00Z","timestamp":1786665600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T00:00:00Z","timestamp":1786665600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T00:00:00Z","timestamp":1786665600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-2153081"],"award-info":[{"award-number":["CHE-2153081"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100007135","name":"University of Tennessee","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100007135","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,27]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Here, we summarize the general use of the symmetry-adapted perturbation theory (SAPT) toward empirical prediction of the energy (and splitting when present) of the Qx- and Qy-bands in a large variety of substituted phthalocyanines (Pcs) and their analogues (i.e., tetraazaporphyrins (TAPs), naphthalocyanines (Ncs), and anthracocyanines (Acs)). It was shown that SAPT can be used as a reliable and quick empirical tool for the accurate (within 0.05 eV) estimation of both Qx- and Qy-band energies and splittings. Simple empirical rules for a 24 nm redshift per added benzene ring at the \u03b2,\u03b2\u2032-positions (96 nm rule going from TAP to Pc to Nc to Ac) and 30, 15, 8, 5, and 4 nm rules for redshift per added amino, thiol, alkoxy, aryl, and alkyl group at the \u03b1-position of the phthalocyanine core, respectively, were established. The SAPT accuracy was tested against the data from more time-consuming and resource-intensive time-dependent density functional theory (TDDFT) calculations for several series of compounds.<\/jats:p>","DOI":"10.1021\/acs.jpca.6c02666","type":"journal-article","created":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T18:01:46Z","timestamp":1786730506000},"page":"6707-6729","source":"Crossref","is-referenced-by-count":0,"title":["From the Four-Orbital\nModel to the Three-Orbital Model:\nParameterizing the\n                    <i>Q<\/i>\n                    <i>x<\/i>\n                    \/\n                    <i>Q<\/i>\n                    <i>y<\/i>\n                    -Band Energies\nin Phthalocyanines and Their Analogues Using Symmetry-Adapted Perturbation\nTheory"],"prefix":"10.1021","volume":"130","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4345-0848","authenticated-orcid":true,"given":"Victor N.","family":"Nemykin","sequence":"first","affiliation":[{"name":"University of Tennessee , , , ,","place":["Knoxville, Tennessee, United States, 37996"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mayra","family":"McKenna","sequence":"additional","affiliation":[{"name":"University of Tennessee , , , ,","place":["Knoxville, Tennessee, United States, 37996"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3654-681X","authenticated-orcid":true,"given":"Brendon J.","family":"McNicholas","sequence":"additional","affiliation":[{"name":"University of Tennessee , , , ,","place":["Knoxville, Tennessee, United States, 37996"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,14]]},"reference":[{"key":"2026090114382196700_cit1","doi-asserted-by":"publisher","first-page":"2709","DOI":"10.1002\/cber.190704002202","article-title":"U\u0308ber die Produkte der Einwirkung von Acetanhydrid\nauf Phthalamid","volume":"40","author":"Braun","year":"1907","journal-title":"Ber. Dtsch. Chem. Ges."},{"key":"2026090114382196700_cit2","doi-asserted-by":"publisher","first-page":"1016","DOI":"10.1039\/jr9340001016","article-title":"212. Phthalocyanines.\nPart I. A new type of synthetic colouring matters","volume":"137","author":"Linstead","year":"1934","journal-title":"J. Chem. Soc."},{"key":"2026090114382196700_cit3","doi-asserted-by":"publisher","first-page":"1017","DOI":"10.1039\/jr9340001017","article-title":"Phthalocyanines. II. The preparation\nof phthalocyanine and some metallic derivatives from o-cyanobenzamide\nand phthalimide","author":"Byrne","year":"1934","journal-title":"J. Chem. Soc."},{"key":"2026090114382196700_cit4","doi-asserted-by":"publisher","first-page":"1022","DOI":"10.1039\/jr9340001022","article-title":"Phthalocyanines.\nIII. Preliminary experiments on the\npreparation of phthalocyanines from phthalonitrile","author":"Linstead","year":"1934","journal-title":"J. Chem. Soc."},{"key":"2026090114382196700_cit5","doi-asserted-by":"publisher","first-page":"165","DOI":"10.1039\/b007515i","article-title":"A tetraazaporphyrin with an intense, broad near-IR\nband","author":"Nemykin","year":"2001","journal-title":"Chem. Commun."},{"key":"2026090114382196700_cit6","doi-asserted-by":"publisher","first-page":"2006","DOI":"10.1021\/ic00037a007","article-title":"Iron octaethyltetraazaporphyrins:\nsynthesis, characterization, coordination chemistry, and comparisons\nto related iron porphyrins and phthalocyanines","volume":"31","author":"Fitzgerald","year":"1992","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit7","doi-asserted-by":"publisher","first-page":"3521","DOI":"10.1039\/jr9550003521","article-title":"Conjugated Macrocycles.\nPart XXVI. Octamethyltetrazaporphin","author":"Baguley","year":"1955","journal-title":"J. Chem.\nSoc."},{"key":"2026090114382196700_cit8","doi-asserted-by":"publisher","first-page":"1931","DOI":"10.1021\/acs.orglett.4c00298","article-title":"Phosphorus(V)\nTetraazaporphyrin with an Intense, Broad\nCT Band in the Near-IR Region","volume":"26","author":"Yoshida","year":"2024","journal-title":"Org. Lett."},{"issue":"7","key":"2026090114382196700_cit9","first-page":"1593","article-title":"Phthalocyanines\nand Related Compounds. XI. Substituted\n2,3-Naphthalocyanines","volume":"42","author":"Kovshev","year":"1972","journal-title":"Zhurnal obshchei khimii"},{"key":"2026090114382196700_cit10","doi-asserted-by":"publisher","first-page":"2235","DOI":"10.1039\/D5NJ04250J","article-title":"Ammonia-free\nand one-pot synthesis of di-chloro silicon\nphthalocyanine and naphthalocyanine","volume":"50","author":"Leshchik","year":"2026","journal-title":"New J.\nChem."},{"key":"2026090114382196700_cit11","doi-asserted-by":"publisher","first-page":"14815","DOI":"10.1039\/D1NJ02793J","article-title":"Photoactive layers for photovoltaics\nbased on near-infrared absorbing aryl-substituted naphthalocyanine\ncomplexes: preparation and investigation of properties","volume":"45","author":"Dubinina","year":"2021","journal-title":"New J. Chem."},{"key":"2026090114382196700_cit12","doi-asserted-by":"publisher","first-page":"64","DOI":"10.1016\/j.poly.2013.04.022","article-title":"The synthesis and\ncharacterization of a group of transition metal octabutoxynaphthalocyanines\nand the absorption and emission properties of the Co, Rh, Ir, Ni,\nPd and Pt members of this group","volume":"57","author":"Kim","year":"2013","journal-title":"Polyhedron"},{"key":"2026090114382196700_cit13","doi-asserted-by":"publisher","first-page":"6294","DOI":"10.1002\/chem.200400275","article-title":"Synthesis, Spectroscopy,\nand Electrochemistry of Tetra-Tert-Butylated Tetraazaporphyrins, Phthalocyanines,\nNaphthalocyanines, and Anthracocyanines, Together with Molecular Orbital\nCalculations","volume":"10","author":"Kobayashi","year":"2004","journal-title":"Chem.\u2500Eur. J."},{"key":"2026090114382196700_cit14","doi-asserted-by":"publisher","first-page":"399","DOI":"10.1246\/cl.1993.399","article-title":"Synthesis\nand characterization of\ntetra(tert-butyl)-2,3-anthracenocyaninatoiron(II) compounds","volume":"22","author":"Hanack","year":"1993","journal-title":"Chem. Lett."},{"key":"2026090114382196700_cit15","doi-asserted-by":"publisher","first-page":"13220","DOI":"10.1039\/C5DT01863C","article-title":"Systematic investigation\nof phthalocyanines, naphthalocyanines, and their aza-analogues. Effect\nof the isosteric aza-replacement in the core","volume":"44","author":"Novakova","year":"2015","journal-title":"Dalton Trans."},{"key":"2026090114382196700_cit16","first-page":"2549","article-title":"Phthalocyanines and related compounds. VII. Tetra-2,3-benzo[g]quinoxalinoporphyrazines","volume":"41","author":"Gal\u2019pern","year":"1971","journal-title":"Zh. Obshch. Khim."},{"key":"2026090114382196700_cit17","first-page":"2536","article-title":"Phthalocyanines and related compounds. III. Synthesis\nand electron absorption spectra of some nitrogen-containing heterocyclic\nanalogs of phthalocyanine","volume":"39","author":"Gal\u2019pern","year":"1969","journal-title":"Zh. Obshch. Khim."},{"key":"2026090114382196700_cit18","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.ccr.2018.01.015","article-title":"Tetrapyrazinoporphyrazines\nand their metal derivatives. Part II: Electronic structure, electrochemical,\nspectral, photophysical and other application related properties","volume":"361","author":"Novakova","year":"2018","journal-title":"Coord. Chem. Rev."},{"key":"2026090114382196700_cit19","doi-asserted-by":"publisher","first-page":"733","DOI":"10.1002\/1099-0682(200103)2001:3&lt;733::AID-EJIC733&gt;3.0.CO;2-2","article-title":"Mossbauer,\ncrystallographic,\nand density functional theoretical investigation of the electronic\nstructure of bis-ligated low-spin iron(II) phthalocyanines","volume":"2001","author":"Nemykin","year":"2001","journal-title":"Eur. J. Inorg. Chem."},{"key":"2026090114382196700_cit20","doi-asserted-by":"publisher","first-page":"87","DOI":"10.1002\/(sici)1099-1409(199902)3:2&lt;87::aid-jpp108&gt;3.0.co;2-g","article-title":"Further\nstudies on the oxidation\nstate of iron in \u03bc-oxo dimeric phthalocyanine complexes","volume":"3","author":"Nemykin","year":"1999","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"2026090114382196700_cit21","doi-asserted-by":"publisher","first-page":"8250","DOI":"10.1021\/acs.inorgchem.2c00721","article-title":"Charge-Transfer\nSpectroscopy of Bisaxially Coordinated Iron(II) Phthalocyanines through\nthe Prism of the Lever\u2032s EL Parameters Scale, MCD\nSpectroscopy, and TDDFT Calculations","volume":"61","author":"Nevonen","year":"2022","journal-title":"Inorg.\nChem."},{"key":"2026090114382196700_cit22","doi-asserted-by":"publisher","first-page":"16626","DOI":"10.1021\/acs.inorgchem.1c02520","article-title":"Application of Lever\u2019s EL Parameter Scale toward Fe(II)\/Fe(III) versus Pc(2-)\/Pc(1-)\nOxidation Process Crossover Point in Axially Coordinated Iron(II)\nPhthalocyanine Complexes","volume":"60","author":"Nemykin","year":"2021","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit23","doi-asserted-by":"publisher","first-page":"3690","DOI":"10.1021\/acs.inorgchem.0c03373","article-title":"Accurate Prediction\nof Mo\u0308ssbauer Hyperfine Parameters\nin Bis-Axially Coordinated Iron(II) Phthalocyanines Using Density\nFunctional Theory Calculations: A Story of a Single Orbital Revealed\nby Natural Bond Orbital Analysis","volume":"60","author":"Nemykin","year":"2021","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit24","doi-asserted-by":"publisher","first-page":"1231","DOI":"10.1142\/S1088424625501056","article-title":"Manganese(III)\nphthalocyanine triflate complexes: Synthesis, structural characterization\nand axial ligand displacement","volume":"29","author":"McKearney","year":"2025","journal-title":"J. Porphyrins\nPhthalocyanines"},{"key":"2026090114382196700_cit25","doi-asserted-by":"publisher","first-page":"6537","DOI":"10.1039\/D4DT00528G","article-title":"Inducing\nring distortions\nin unsubstituted metallophthalocyanines using axial N-heterocyclic\ncarbenes","volume":"53","author":"Kidd","year":"2024","journal-title":"Dalton Trans."},{"key":"2026090114382196700_cit26","doi-asserted-by":"publisher","first-page":"5350","DOI":"10.1021\/ic011152d","article-title":"Electronic Structure\nof Reduced Symmetry Peripheral Fused-Ring-Substituted Phthalocyanines","volume":"41","author":"Kobayashi","year":"2002","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit27","doi-asserted-by":"publisher","first-page":"15139","DOI":"10.1021\/acs.inorgchem.5c02142","article-title":"Puzzle\nof Phosphorus(V) Phthalocyanine Distortion: Crystallographic vs Computational\nViewpoints","volume":"64","author":"Sinelshchikova","year":"2025","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit28","doi-asserted-by":"publisher","DOI":"10.1016\/j.inoche.2026.116513","article-title":"The key\nto the phosphorus heart:\nmild axial mono-functionalization of phosphorus(V) phthalocyanines","volume":"188","author":"Ovchenkova","year":"2026","journal-title":"Inorg. Chem. Commun."},{"key":"2026090114382196700_cit29","doi-asserted-by":"publisher","first-page":"9549","DOI":"10.1021\/acs.inorgchem.6b00992","article-title":"Tuning\nUp an Electronic Structure of the Subphthalocyanine Derivatives toward\nElectron-Transfer Process in Noncovalent Complexes with C60 and C70 Fullerenes: Experimental and Theoretical Studies","volume":"55","author":"Rhoda","year":"2016","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit30","doi-asserted-by":"publisher","first-page":"8362","DOI":"10.1021\/ic3008798","article-title":"Insight into the Electronic Structure,\nOptical Properties, And Redox Behavior of the Hybrid Phthalocyaninoclathrochelates\nfrom Experimental and Density Functional Theory Approaches","volume":"51","author":"Sabin","year":"2012","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit31","doi-asserted-by":"publisher","first-page":"432","DOI":"10.1002\/(SICI)1099-1409(200006\/07)4:4&lt;432::SID-JPP254&gt;3.0.CO;2-N","article-title":"Industrial\napplications of phthalocyanines","volume":"4","author":"Gregory","year":"2000","journal-title":"J. Porphyrins\nPhthalocyanines"},{"key":"2026090114382196700_cit32","doi-asserted-by":"publisher","first-page":"733","DOI":"10.1002\/adsc.200800784","article-title":"Comparative reactivity\nof hypervalent iodine oxidants\nin metalloporphyrin-catalyzed oxygenation of hydrocarbons: iodosylbenzene\nsulfate and 2-iodylbenzoic acid ester as safe and convenient alternatives\nto iodosylbenzene","volume":"351","author":"Geraskin","year":"2009","journal-title":"Adv. Synth. Catalysis"},{"key":"2026090114382196700_cit33","doi-asserted-by":"publisher","first-page":"6545","DOI":"10.1016\/j.tetlet.2010.10.023","article-title":"Binuclear\niron(III) phthalocyanine(\u03bc-oxodimer)\/tetrabutylammonium\noxone: a powerful catalytic system for oxidation of hydrocarbons in\norganic solution","volume":"51","author":"Neu","year":"2010","journal-title":"Tetr. Lett."},{"key":"2026090114382196700_cit34","doi-asserted-by":"publisher","first-page":"5687","DOI":"10.1016\/j.tetlet.2014.08.070","article-title":"Binuclear iron(III)\noctakis(perfluorophenyl)tetraazaporphyrin\n\u03bc-oxodimer: a highly efficient catalyst for biomimetic oxygenation\nreactions","volume":"55","author":"Yusubov","year":"2014","journal-title":"Tetr. Lett."},{"key":"2026090114382196700_cit35","doi-asserted-by":"publisher","first-page":"4984","DOI":"10.1021\/acscatal.4c07696","article-title":"Designing Ruthenium\nPhthalocyanine with Chiral Pockets Formed by (1R,2S,5R)-Menthoxy Groups\nfor Enantioselective Catalysis","volume":"15","author":"Kroitor","year":"2025","journal-title":"ACS Catal."},{"key":"2026090114382196700_cit36","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2025.116443","article-title":"How far\nis far? Weak noncovalent interactions govern enantioselective cyclopropanation\ncatalyzed by ruthenium phthalocyanine with remote (R)-BINOL substituents","volume":"452","author":"Dmitrienko","year":"2025","journal-title":"J. Catal."},{"key":"2026090114382196700_cit37","doi-asserted-by":"publisher","first-page":"4018","DOI":"10.1039\/D4DT03263B","article-title":"Non-aggregated\nruthenium naphthalocyanine enabling homogeneous carbene insertion\ninto N-H bonds at low catalyst loading","volume":"54","author":"Kroitor","year":"2025","journal-title":"Dalton\nTrans."},{"key":"2026090114382196700_cit38","doi-asserted-by":"publisher","first-page":"6939","DOI":"10.1021\/jacs.5c16528","article-title":"Concerted Proton-Electron Transfer\nMinimizes Substituent\nEffects on Adsorbed Phthalocyanine Electrocatalysis","volume":"148","author":"Mannava","year":"2026","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114382196700_cit39","doi-asserted-by":"publisher","first-page":"50692","DOI":"10.1039\/D5RA06357D","article-title":"Phthalocyanine-based\ncovalent organic frameworks: bridging molecular design and catalytic\nperformance in CO2 reduction","volume":"15","author":"Li","year":"2025","journal-title":"RSC\nAdv."},{"key":"2026090114382196700_cit40","doi-asserted-by":"publisher","first-page":"12390","DOI":"10.1021\/acs.inorgchem.5c02178","article-title":"Fullerene\nPromotes CO2 Reduction to Methanol by a Cobalt(II) Phthalocyanine\nElectrocatalyst","volume":"64","author":"Fosu","year":"2025","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit41","doi-asserted-by":"publisher","first-page":"1429","DOI":"10.1351\/pac199668071429","article-title":"Macrocyclic\nfunctional dyes: applications to optical\ndisk media, photochemical hole burning and nonlinear optics","volume":"68","author":"Seto","year":"1996","journal-title":"Pure Appl. Chem."},{"key":"2026090114382196700_cit42","doi-asserted-by":"publisher","first-page":"125","DOI":"10.1016\/0030-4018(95)00524-4","article-title":"Application of phthalocyanine thin films in optical\nrecording","volume":"121","author":"Gu","year":"1995","journal-title":"Opt. Commun."},{"key":"2026090114382196700_cit43","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.ccr.2018.10.007","article-title":"Phthalocyanines for\ndye-sensitized solar cells","volume":"381","author":"Urbani","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"2026090114382196700_cit44","doi-asserted-by":"publisher","first-page":"2738","DOI":"10.1039\/C9CS00059C","article-title":"Phthalocyanines and\nporphyrinoid analogues as hole- and electron-transporting materials\nfor perovskite solar cells","volume":"48","author":"Urbani","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"2026090114382196700_cit45","doi-asserted-by":"publisher","first-page":"18760","DOI":"10.1002\/chem.201603705","article-title":"Low-Symmetry \u03a9-Shaped Zinc\nPhthalocyanine Sensitizers\nhaving Panchromatic Light-Harvesting Property for Dye-Sensitized Solar\nCells","volume":"22","author":"Yamamoto","year":"2016","journal-title":"Chem.\u2500Eur. J."},{"key":"2026090114382196700_cit46","doi-asserted-by":"publisher","first-page":"1809","DOI":"10.1021\/ar900034t","article-title":"Large \u03c0-Aromatic Molecules\nas Potential Sensitizers for Highly Efficient Dye-Sensitized Solar\nCells","volume":"42","author":"Imahori","year":"2009","journal-title":"Acc. Chem. Res."},{"key":"2026090114382196700_cit47","doi-asserted-by":"publisher","first-page":"86","DOI":"10.1002\/cssc.201701441","article-title":"Near-Infrared-Absorbing\nMetal-Free\nOrganic, Porphyrin, and Phthalocyanine Sensitizers for Panchromatic\nDye-Sensitized Solar Cells","volume":"11","author":"Brogdon","year":"2018","journal-title":"ChemSusChem"},{"key":"2026090114382196700_cit48","doi-asserted-by":"publisher","first-page":"6049","DOI":"10.1007\/s11664-024-11324-1","article-title":"Effects of\nMetal Phthalocyanine and\nNaphthalocyanine on Perovskite Solar Cells","volume":"53","author":"Suzuki","year":"2024","journal-title":"J. Electron. Mater."},{"key":"2026090114382196700_cit49","doi-asserted-by":"publisher","first-page":"5638","DOI":"10.1021\/jp400046b","article-title":"Self-Assembled via Metal-Ligand Coordination\nAzaBODIPY-Zinc\nPhthalocyanine and AzaBODIPY-Zinc Naphthalocyanine Conjugates: Synthesis,\nStructure, and Photoinduced Electron Transfer","volume":"117","author":"Bandi","year":"2013","journal-title":"J. Phys. Chem. C"},{"key":"2026090114382196700_cit50","doi-asserted-by":"publisher","DOI":"10.1002\/cptc.202500238","article-title":"Zinc Phthalocyanine N-Linked to Pyrroloperylenediimide\nDyad: Significance of N-Connectivity in Modulating Photodynamics Toward\nProlonging the Lifetime of Charge Separation","volume":"10","author":"Ileperuma","year":"2026","journal-title":"ChemPhotoChem"},{"key":"2026090114382196700_cit51","doi-asserted-by":"publisher","first-page":"11004","DOI":"10.1021\/ic4011423","article-title":"Probing the Electronic\nProperties of a Trinuclear Molecular Wire Involving Isocyanoferrocene\nand Iron(II) Phthalocyanine Motifs","volume":"52","author":"Nemykin","year":"2013","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit52","doi-asserted-by":"publisher","first-page":"900","DOI":"10.1021\/ar5004384","article-title":"Phthalocyanine-Nanocarbon Ensembles:\nFrom Discrete Molecular and Supramolecular Systems to Hybrid Nanomaterials","volume":"48","author":"Bottari","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"2026090114382196700_cit53","doi-asserted-by":"publisher","first-page":"1877","DOI":"10.1039\/b800617b","article-title":"Modulating the electronic properties\nof porphyrinoids: a voyage from the violet to the infrared regions\nof the electromagnetic spectrum","volume":"6","author":"Rio","year":"2008","journal-title":"Org. Biomol.\nChem."},{"key":"2026090114382196700_cit54","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1142\/S1088424624500329","article-title":"Quantifying\nthe effects of peripheral substituents\non the spin-lattice relaxation of a vanadyl molecular quantum bit","volume":"28","author":"Lohaus","year":"2024","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"2026090114382196700_cit55","doi-asserted-by":"publisher","first-page":"9252","DOI":"10.1021\/acs.jpca.0c07860","article-title":"Understanding\nCovalent versus Spin-Orbit Coupling Contributions to Temperature-Dependent\nElectron Spin Relaxation in Cupric and Vanadyl Phthalocyanines","volume":"124","author":"Follmer","year":"2020","journal-title":"J. Phys. Chem. A"},{"key":"2026090114382196700_cit56","doi-asserted-by":"publisher","first-page":"2605","DOI":"10.3390\/ijms25052605","article-title":"Dual Emissive\nZn(II) Naphthalocyanines: Synthesis, Structural and Photophysical\nCharacterization with Theory-Supported Insights towards Soluble Coordination\nCompounds with Visible and Near-Infrared Emission","volume":"25","author":"Sailaja","year":"2024","journal-title":"Int. J. Mol. Sci."},{"key":"2026090114382196700_cit57","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2025.126869","article-title":"Cobalt phthalocyanine\nencapsulation boosts oxidase-like activity of single-atom Co-N-C nanozyme\nfor fluorescence sensing of tetracycline","volume":"346","author":"Xiao","year":"2026","journal-title":"Spectrochim.\nActa, Part A"},{"key":"2026090114382196700_cit58","doi-asserted-by":"publisher","first-page":"8440","DOI":"10.1002\/anie.202000108","article-title":"Design of Turn-On Near-Infrared Fluorescent Probes\nfor Highly Sensitive and Selective Monitoring of Biopolymers","volume":"59","author":"Ducharme","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114382196700_cit59","doi-asserted-by":"publisher","first-page":"1552","DOI":"10.1021\/acssensors.9b00081","article-title":"Red-Emitting Fluorescence\nSensors for Metal Cations: The Role of Counteranions and Sensing of\nSCN\u2013 in Biological Materials","volume":"4","author":"Lochman","year":"2019","journal-title":"ACS Sens."},{"key":"2026090114382196700_cit60","doi-asserted-by":"publisher","first-page":"5777","DOI":"10.1021\/acs.analchem.9b00010","article-title":"Ultrasensitive Sensor\nUsing Quantum Dots-Doped Polystyrene Nanospheres for Clinical Diagnostics\nof Low-Volume Serum Samples","volume":"91","author":"Chen","year":"2019","journal-title":"Anal. Chem."},{"key":"2026090114382196700_cit61","doi-asserted-by":"publisher","DOI":"10.1016\/j.jinorgbio.2019.110793","article-title":"Binding and photodynamic\naction of the cationic zinc phthalocyanines with different types of\nDNA toward understanding of their cancer therapy activity","volume":"199","author":"McRae","year":"2019","journal-title":"J. Inorg. Biochem."},{"key":"2026090114382196700_cit62","doi-asserted-by":"publisher","first-page":"1041","DOI":"10.1039\/C9CS00129H","article-title":"The unique\nfeatures and promises of phthalocyanines\nas advanced photosensitisers for photodynamic therapy of cancer","volume":"49","author":"Lo","year":"2020","journal-title":"Chem. Soc. Rev."},{"key":"2026090114382196700_cit63","doi-asserted-by":"publisher","first-page":"983","DOI":"10.1007\/s12551-023-01129-7","article-title":"Phthalocyanine\naggregates in the photodynamic therapy: dogmas, controversies, and\nfuture prospects","volume":"15","author":"Bunin","year":"2023","journal-title":"Biophys. Rev."},{"key":"2026090114382196700_cit64","doi-asserted-by":"publisher","first-page":"658","DOI":"10.1021\/acs.jmedchem.4c02451","article-title":"Pivotal\nRole of the Intracellular Microenvironment in the High Photodynamic\nActivity of Cationic Phthalocyanines","volume":"68","author":"Bunin","year":"2025","journal-title":"J. Med.\nChem."},{"key":"2026090114382196700_cit65","doi-asserted-by":"publisher","DOI":"10.1016\/j.optmat.2025.117831","article-title":"Monomeric\nvs. aggregated phthalocyanine photosensitizers: differentiation between\nI and II type of photoreactions","volume":"172","author":"Bunin","year":"2026","journal-title":"Opt. Mater."},{"key":"2026090114382196700_cit66","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochemrev.2021.100422","article-title":"Overview of cationic\nphthalocyanines\nfor effective photoinactivation of pathogenic microorganisms","volume":"48","author":"Ribeiro","year":"2021","journal-title":"J. Photochem. Photobiol., C"},{"key":"2026090114382196700_cit67","doi-asserted-by":"publisher","first-page":"399","DOI":"10.1142\/S1088424613300024","article-title":"Metallophthalocyanines\nfor antimicrobial photodynamic therapy: an overview of our experience","volume":"17","author":"Mantareva","year":"2013","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"2026090114382196700_cit68","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2025.216969","article-title":"Structure-property relationships\nof main-group element phthalocyanines in photo\/sono-driven cancer\ntherapy","volume":"544","author":"Liu","year":"2025","journal-title":"Coord. Chem. Rev."},{"key":"2026090114382196700_cit69","doi-asserted-by":"publisher","first-page":"1077","DOI":"10.1016\/j.apsb.2023.11.030","article-title":"Design consideration\nof phthalocyanines as sensitizers\nfor enhanced sono-photodynamic combinatorial therapy of cancer","volume":"14","author":"Nene","year":"2024","journal-title":"Acta Pharm. Sinica B"},{"key":"2026090114382196700_cit70","doi-asserted-by":"publisher","first-page":"10261","DOI":"10.1021\/acs.chemrev.5b00244","article-title":"Glycosylated Porphyrins, Phthalocyanines,\nand Other Porphyrinoids for Diagnostics and Therapeutics","volume":"115","author":"Singh","year":"2015","journal-title":"Chem. Rev."},{"key":"2026090114382196700_cit71","doi-asserted-by":"publisher","first-page":"1249","DOI":"10.1142\/S1088424625501093","article-title":"Spectral\nproperties,\nelectronic states, and aggregation of highly-fluorinated zinc phthalocyanines","volume":"29","author":"Chan","year":"2025","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"2026090114382196700_cit72","doi-asserted-by":"publisher","first-page":"281","DOI":"10.1021\/cr9003049","article-title":"Low symmetry\nphthalocyanines and their analogues","volume":"111","author":"Mack","year":"2011","journal-title":"Chem. Rev."},{"key":"2026090114382196700_cit73","doi-asserted-by":"publisher","first-page":"649","DOI":"10.1142\/S108842461330005X","article-title":"Routes to some 3,6-disubstituted\nphthalonitriles and examples of phthalocyanines derived therefrom:\nAn overview","volume":"17","author":"Heeney","year":"2013","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"2026090114382196700_cit74","first-page":"1","volume-title":"Handbook of Porphyrin\nScience","author":"Fukuda","year":"2010"},{"key":"2026090114382196700_cit75","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1142\/S1088424610001799","article-title":"The key role of peripheral substituents in the chemistry\nof phthalocyanines and their analogs","volume":"14","author":"Lukyanets","year":"2010","journal-title":"J. Porphyrins\nPhthalocyanines"},{"issue":"(i)","key":"2026090114382196700_cit76","doi-asserted-by":"publisher","first-page":"136","DOI":"10.3998\/ark.5550190.0011.104","article-title":"Synthesis of substituted phthalocyanines","volume":"2010","author":"Nemykin","year":"2010","journal-title":"ARKIVOC"},{"key":"2026090114382196700_cit77","first-page":"1","volume-title":"Handbook of Porphyrin\nScience","author":"Nemykin","year":"2010"},{"key":"2026090114382196700_cit78","doi-asserted-by":"publisher","first-page":"1134","DOI":"10.1142\/S1088424611004269","article-title":"Application of magnetic circular dichroism spectroscopy\nto porphyrins, phthalocyanines and hemes","volume":"15","author":"Tiedemann","year":"2011","journal-title":"J.\nPorphyrins Phthalocyanines"},{"key":"2026090114382196700_cit79","doi-asserted-by":"publisher","first-page":"108","DOI":"10.1016\/0022-2852(63)90011-0","article-title":"Spectra of Porphyrins:\nPart II. Four\nOrbital Model","volume":"11","author":"Gouterman","year":"1963","journal-title":"J. Mol. Spectrosc."},{"key":"2026090114382196700_cit80","doi-asserted-by":"publisher","first-page":"138","DOI":"10.1016\/0022-2852(61)90236-3","article-title":"Spectra of\nPorphyrins","volume":"6","author":"Gouterman","year":"1961","journal-title":"J. Mol. Spectrosc."},{"key":"2026090114382196700_cit81","doi-asserted-by":"publisher","first-page":"12901","DOI":"10.1021\/jp0759731","article-title":"Influence\nof Molecular Geometry, Exchange-Correlation Functional, and Solvent\nEffects in the Modeling of Vertical Excitation Energies in Phthalocyanines\nUsing Time-Dependent Density Functional Theory (TDDFT) and Polarized\nContinuum Model TDDFT Methods: Can Modern Computational Chemistry\nMethods Explain Experimental Controversies?","volume":"111","author":"Nemykin","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"2026090114382196700_cit82","doi-asserted-by":"publisher","first-page":"7265","DOI":"10.1021\/acsomega.8b03500","article-title":"Methodological Survey of Simplified TD-DFT Methods\nfor Fast and Accurate Interpretation of UV-Vis-NIR Spectra of Phthalocyanines","volume":"4","author":"Martynov","year":"2019","journal-title":"ACS Omega"},{"key":"2026090114382196700_cit83","doi-asserted-by":"publisher","first-page":"993","DOI":"10.1016\/S0010-8545(01)00394-0","article-title":"Assignment of the optical spectra\nof metal phthalocyanines\nthrough spectral band deconvolution analysis and ZINDO calculations","volume":"219\u2013221","author":"Mack","year":"2001","journal-title":"Coord. Chem. Rev."},{"key":"2026090114382196700_cit84","doi-asserted-by":"publisher","first-page":"321","DOI":"10.3987\/COM-07-S(W)8","article-title":"Electronic\nstructures and molecular orbital calculations of oppositely dinaphthalo-\nand dianthraco-substituted D2h type metal-free phthalocyanine\ncongeners","volume":"74","author":"Matsushita","year":"2007","journal-title":"Heterocycles"},{"key":"2026090114382196700_cit85","doi-asserted-by":"publisher","first-page":"132","DOI":"10.1021\/acs.jpca.8b07647","article-title":"Simultaneous\nPrediction of the Energies of Qx and Qy Bands and Intramolecular Charge-Transfer\nTransitions in Benzoannulated and Non-Peripherally Substituted Metal-Free\nPhthalocyanines and Their Analogues: No Standard TDDFT Silver Bullet\nYet","volume":"123","author":"Belosludov","year":"2019","journal-title":"J. Phys. Chem. A"},{"key":"2026090114382196700_cit86","doi-asserted-by":"publisher","first-page":"122","DOI":"10.1016\/j.jinorgbio.2014.01.001","article-title":"MCD spectroscopy and TD-DFT calculations\nof low symmetry\nsubnaphthalocyanine analogs","volume":"136","author":"Mack","year":"2014","journal-title":"J. Inorg. Biochem."},{"key":"2026090114382196700_cit87","doi-asserted-by":"publisher","first-page":"17697","DOI":"10.1021\/ja0540728","article-title":"Application of MCD\nSpectroscopy and TD-DFT to a Highly Non-Planar Porphyrinoid Ring System.\nNew Insights on Red-Shifted Porphyrinoid Spectral Bands","volume":"127","author":"Mack","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114382196700_cit88","doi-asserted-by":"publisher","first-page":"1163","DOI":"10.1139\/cjc-2016-0264","article-title":"CASSCF-based explicit ligand field\nmodels clarify the ground state electronic structures of transition\nmetal phthalocyanines (MPc; M = Mn, Fe, Co, Ni, Cu, Zn)","volume":"94","author":"Wallace","year":"2016","journal-title":"Can. J. Chem."},{"key":"2026090114382196700_cit89","doi-asserted-by":"publisher","first-page":"429","DOI":"10.1016\/j.ccr.2006.05.011","article-title":"Application of MCD spectroscopy to\nporphyrinoids","volume":"251","author":"Mack","year":"2007","journal-title":"Coord. Chem. Rev."},{"key":"2026090114382196700_cit90","doi-asserted-by":"publisher","first-page":"812","DOI":"10.1021\/ic0009829","article-title":"Transition Assignments\nin the Ultraviolet-Visible Absorption\nand Magnetic Circular Dichroism Spectra of Phthalocyanines","volume":"40","author":"Mack","year":"2001","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit91","doi-asserted-by":"publisher","first-page":"790","DOI":"10.1039\/f29747000790","article-title":"Assignment of the charge-transfer bands in metal phthalocyanines.\nEvidence for the S = 1 state of iron(II) phthalocyanine in solution","volume":"70","author":"Stillman","year":"1974","journal-title":"J. Chem. Soc., Faraday Trans. 2"},{"issue":"11","key":"2026090114382196700_cit92","doi-asserted-by":"publisher","first-page":"1236","DOI":"10.1246\/cl.2000.1236","article-title":"Diels-Alder\nreaction of tribenzo[b,g,l]thiopheno[3,4-q]porphyrazine\nas a new path for porphyrazine core modification","volume":"29","author":"Nemykin","year":"2000","journal-title":"Chem. Lett."},{"key":"2026090114382196700_cit93","doi-asserted-by":"publisher","first-page":"3632","DOI":"10.1021\/ic991496s","article-title":"Band Deconvolution Analysis of the\nAbsorption and Magnetic Circular Dichroism Spectral Data of a Planar\nPhthalocyanine Dimer","volume":"39","author":"Kobayashi","year":"2000","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit94","doi-asserted-by":"publisher","first-page":"164","DOI":"10.1021\/ic801552u","article-title":"Synthesis\nand Spectroscopic and Electrochemical Studies of Pyrazine- or Pyridine-Ring-Fused\nTetraazachlorins, Bacteriochlorins, and Isobacteriochlorins","volume":"48","author":"Makarova","year":"2009","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit95","doi-asserted-by":"publisher","first-page":"1139","DOI":"10.1063\/1.1730148","article-title":"Study of the\nEffects of Substitution on the Absorption Spectra of Porphin","volume":"30","author":"Gouterman","year":"1959","journal-title":"J. Chem. Phys."},{"key":"2026090114382196700_cit96","doi-asserted-by":"publisher","first-page":"153","DOI":"10.1080\/00268979300102141","article-title":"Electronic\nspectra of beno-substituted phthalocyanines","volume":"80","author":"Konami","year":"1993","journal-title":"Mol. Phys."},{"key":"2026090114382196700_cit97","doi-asserted-by":"publisher","first-page":"763","DOI":"10.1246\/cl.1992.763","article-title":"Synthesis\nof Non-Symmetrically Benzo-Substituted Phthalocyanines and Their Electronic\nSpectra","volume":"21","author":"Ikeda","year":"1992","journal-title":"Chem. Lett."},{"key":"2026090114382196700_cit98","first-page":"349","volume-title":"Phthalocyanines: Properties\nand Applications","author":"Kobayashi","year":"1996"},{"key":"2026090114382196700_cit99","doi-asserted-by":"publisher","first-page":"742","DOI":"10.1002\/jpp.391","article-title":"Position isomer separation of non-peripheral\nsubstituted zinc dibenzo-di(3,4-pyrido)porphyrazines","volume":"05","author":"Sakamoto","year":"2001","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"2026090114382196700_cit100","doi-asserted-by":"publisher","first-page":"770","DOI":"10.1021\/ja01221a022","article-title":"Rules for\nthe absorption spectra of dyes","volume":"67","author":"Lewis","year":"1945","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026090114382196700_cit101","doi-asserted-by":"publisher","first-page":"165","DOI":"10.1002\/bbpc.19490530315","article-title":"Theoretical\ninterpretation of the light absorption of organic dyes","volume":"53","author":"Kuhn","year":"1949","journal-title":"Z. Elektrochem."},{"key":"2026090114382196700_cit102","doi-asserted-by":"publisher","first-page":"1617","DOI":"10.1039\/jr9540001617","article-title":"Calculations of bond orders, resonance\nenergies, and orbital energies by a simple perturbation method","author":"Dewar","year":"1954","journal-title":"J. Chem. Soc."},{"key":"2026090114382196700_cit103","unstructured":"Atkins, P. W.\n          \n          Molecular Quantum\nMechanics, Oxford, NY, 1983."},{"key":"2026090114382196700_cit104","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2020.213605","article-title":"An exciting\ntwenty-year journey exploring porphyrinoid-based photo- and electro-active\nsystems","volume":"428","author":"Bottari","year":"2021","journal-title":"Coord. Chem. Rev."},{"key":"2026090114382196700_cit105","doi-asserted-by":"publisher","first-page":"8049","DOI":"10.1039\/c3cs60140d","article-title":"A voyage into the synthesis\nand photophysics\nof homo- and heterobinuclear ensembles of phthalocyanines and porphyrins","volume":"42","author":"de la Torre","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"2026090114382196700_cit106","doi-asserted-by":"publisher","first-page":"1422","DOI":"10.1002\/anie.199314221","article-title":"Chromatographic\nseparation of the four possible constitutional isomers of a tetrasubstituted\nphthalocyanine: tetrakis[(2-ethylhexyl)oxy]phthalocyaninatonickel(II)","volume":"32","author":"Hanack","year":"1993","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114382196700_cit107","doi-asserted-by":"publisher","first-page":"58","DOI":"10.1039\/c39930000058","article-title":"Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II)","author":"Hanack","year":"1993","journal-title":"J. Chem. Soc., Chem. Commun."},{"key":"2026090114382196700_cit108","doi-asserted-by":"publisher","first-page":"1990","DOI":"10.1139\/v94-254","article-title":"The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines","volume":"72","author":"Leznoff","year":"1994","journal-title":"Can. J. Chem."},{"issue":"i","key":"2026090114382196700_cit109","doi-asserted-by":"publisher","first-page":"142","DOI":"10.3998\/ark.5550190.p008.412","article-title":"Synthetic approaches to asymmetric\nphthalocyanines and their analogues","volume":"2014","author":"Nemykin","year":"2014","journal-title":"ARKIVOC"},{"key":"2026090114382196700_cit110","doi-asserted-by":"publisher","first-page":"4015","DOI":"10.1021\/ic50225a088","article-title":"Electrochemistry of main-group phthalocyanines","volume":"20","author":"Lever","year":"1981","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit111","doi-asserted-by":"publisher","first-page":"79","DOI":"10.1126\/science.1059552","article-title":"Fully Conjugal Porphyrin Tapes with\nElectronic Absorption Bands that Reach into Infrared","volume":"293","author":"Tsuda","year":"2001","journal-title":"Science"},{"key":"2026090114382196700_cit112","doi-asserted-by":"publisher","first-page":"2480","DOI":"10.1021\/acs.jpca.1c00217","article-title":"Accurate Prediction\nof the Excited States in the Fully Conjugated Porphyrin Tapes across\nthe Full Spectral Range: A Story of the Interplay between \u03c0-\u03c0*\nand Intramolecular Charge-Transfer Transitions in Soft Chromophores","volume":"125","author":"Belosludov","year":"2021","journal-title":"J. Phys. Chem. A"},{"key":"2026090114382196700_cit113","doi-asserted-by":"publisher","first-page":"8007","DOI":"10.1021\/ja0123812","article-title":"Adjacent versus\nOpposite Type Di-Aromatic Ring-Fused Phthalocyanine Derivatives: Synthesis,\nSpectroscopy, Electrochemistry, and Molecular Orbital Calculations","volume":"124","author":"Kobayashi","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114382196700_cit114","doi-asserted-by":"publisher","first-page":"2031","DOI":"10.1246\/cl.1992.2031","article-title":"Synthesis, spectroscopy,\nelectrochemistry, and spectroelectrochemistry of a zinc phthalocyanine\nwith D2h symmetry","volume":"21","author":"Kobayashi","year":"1992","journal-title":"Chem. Lett."},{"issue":"2","key":"2026090114382196700_cit115","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1070\/MC1995v005n02ABEH000464","article-title":"New, non-symmetrical 2:2 phthalocyanines. 1,2,3,4,15,16,17,18-Octaphenyl-9\u201323(24)-dinitrophthalo-\nand 1,2,3,4,19,20,21,22-octaphenyldiphthalo-11,29(30)-di-tert-butyldinaphthalocyanine\ncopper complexes","volume":"5","author":"Nemykin","year":"1995","journal-title":"Mendeleev Commun."},{"key":"2026090114382196700_cit116","doi-asserted-by":"publisher","first-page":"121","DOI":"10.1070\/MC1993v003n03ABEH000253","article-title":"A synthesis\nof novel\nnon-symmetrical phthalocyanines","volume":"3","author":"Subbotin","year":"1993","journal-title":"Mendeleev Commun."},{"key":"2026090114382196700_cit117","doi-asserted-by":"publisher","first-page":"2051","DOI":"10.1002\/cber.19941271030","article-title":"Synthesis, separation\nand characterization\nof unsymmetrically substituted phthalocyanines","volume":"127","author":"Lin\u00dfen","year":"1994","journal-title":"Chem. Ber."},{"key":"2026090114382196700_cit118","doi-asserted-by":"publisher","first-page":"233","DOI":"10.1002\/adfm.200390035","article-title":"Mono-Bisthienylethene\nRing-Fused versus Multi-Bisthienylethene Ring-Fused Photochromic Hybrids","volume":"13","author":"Luo","year":"2003","journal-title":"Adv. Funct. Mater."},{"key":"2026090114382196700_cit119","doi-asserted-by":"publisher","first-page":"1129","DOI":"10.1142\/s1088424604000490","article-title":"The chemistry of\nporphyrazines: an overview","volume":"08","author":"Rodri\u0301guez-Morgade","year":"2004","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"2026090114382196700_cit120","doi-asserted-by":"publisher","first-page":"2655","DOI":"10.1021\/ic970018j","article-title":"Synthesis\nand Spectral\nProperties of Bisaxially Coordinated (Octaphenyltetraazaporphyrinato)ruthenium(II)\nComplexes","volume":"37","author":"Stuzhin","year":"1998","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit121","doi-asserted-by":"publisher","first-page":"114","DOI":"10.6060\/mhc2009.2.114","article-title":"Iron complexes of octaphenyltetraazaporphine","volume":"2","author":"Stuzhin","year":"2009","journal-title":"Makrogeterotsikly"},{"key":"2026090114382196700_cit122","doi-asserted-by":"publisher","first-page":"11563","DOI":"10.1039\/C6CC06344F","article-title":"NIR absorbing diferrocene-containing\nmeso-cyano-BODIPY with a UV-Vis-NIR spectrum remarkably close to that\nof magnesium tetracyanotetraferrocenyltetraazaporphyrin","volume":"52","author":"Didukh","year":"2016","journal-title":"Chem. Commun."},{"key":"2026090114382196700_cit123","doi-asserted-by":"publisher","first-page":"248","DOI":"10.1002\/(SICI)1099-1409(200004\/05)4:3&lt;248::AID-JPP202&gt;3.3.CO;2-N","article-title":"Towards chiral\n1,2-naphthalocyanines: synthesis of the pure geometrical\nisomers of the magnesium and lutetium complexes","volume":"4","author":"Negrimovskii","year":"2000","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"2026090114382196700_cit124","doi-asserted-by":"publisher","first-page":"12820","DOI":"10.1021\/ic301712h","article-title":"Synthesis,\ncharacterization, MCD spectroscopy, and TD-DFT calculations of copper-metalated\nnonperipherally substituted octaoctyl derivatives of tetrabenzoporphyrin,\ncis- and trans-tetradibenzodiazaporphyrin, tetrabenzomonoazaporphyrin,\nand tetrabenzoporphyrin","volume":"51","author":"Mack","year":"2012","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit125","doi-asserted-by":"publisher","first-page":"3136","DOI":"10.1002\/chem.201002176","article-title":"Phthalocyanine\nanalogues: unexpectedly\nfacile access to non-peripherally substituted octaalkyl tetrabenzoporphyrins,\ntetrabenzodiazaporphyrins, tetrabenzomonoazaporphyrins and tetrabenzoporphyrins","volume":"17","author":"Cammidge","year":"2011","journal-title":"Chem.\u2500Eur. J."},{"key":"2026090114382196700_cit126","doi-asserted-by":"publisher","first-page":"146401\/1","DOI":"10.1103\/PhysRevLett.91.146401","article-title":"Climbing the Density\nFunctional Ladder: Nonempirical\nMeta-Generalized Gradient Approximation Designed for Molecules and\nSolids","volume":"91","author":"Tao","year":"2003","journal-title":"Phys. Rev. Lett."},{"key":"2026090114382196700_cit127","doi-asserted-by":"publisher","first-page":"1033","DOI":"10.1063\/1.1673095","article-title":"Gaussian Basis Set for Molecular\nWavefunctions Containing\nThird-Row Atoms","volume":"52","author":"Wachters","year":"1970","journal-title":"J. Chem. Phys."},{"key":"2026090114382196700_cit128","doi-asserted-by":"publisher","first-page":"5639","DOI":"10.1063\/1.438980","article-title":"Contracted Gaussian asis set for\nmolecular calculations. I. Second row atoms, Z = 11\u201318","volume":"72","author":"McLean","year":"1980","journal-title":"J. Chem. Phys."},{"key":"2026090114382196700_cit129","doi-asserted-by":"publisher","first-page":"2999","DOI":"10.1021\/cr9904009","article-title":"Quantum Mechanical\nContinuum Solvation Models","volume":"105","author":"Tomasi","year":"2005","journal-title":"Chem. Rev."},{"key":"2026090114382196700_cit130","unstructured":"Frisch, M. J.; Trucks, D. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams-Young, D.; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery Jr, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; Foresman, J. B.; Fox, D. J.\n          Gaussian 16, Revision B.01; Gaussian, Inc.: Wallingford CT, 2016."},{"key":"2026090114382196700_cit131","doi-asserted-by":"publisher","first-page":"475","DOI":"10.1007\/BF00810897","article-title":"Synthese von\nMetallkomplexen des\nTetra-(2,3-anthra)-tetraazaporphins und Vergleich ihrer Elektronenabsorptionsspektren\nmit denen anderer anellierter Tetraazaporphinsysteme","volume":"117","author":"Freyer","year":"1986","journal-title":"Monatsh. Chem."},{"key":"2026090114382196700_cit132","doi-asserted-by":"publisher","first-page":"2466","DOI":"10.1039\/JR9570002466","article-title":"481. Conjugated\nMacrocycles. Part XXIX. Tribenzotetrazaporphin Metal Derivatives and\nDibromotribenzotetrazaporphin","author":"Elvidge","year":"1957","journal-title":"J. Chem. Soc."},{"key":"2026090114382196700_cit133","first-page":"696","article-title":"Phthalocyanines and\nrelated compounds. X. Synthesis and electronic absorption spectra\nof tetra-6-tert-butyl-2,3-naphthalocyanines","volume":"42","author":"Kovshev","year":"1972","journal-title":"Zh. Obshch. Khim."},{"issue":"No.","key":"2026090114382196700_cit134","doi-asserted-by":"publisher","first-page":"866","DOI":"10.1039\/JR9610000866","article-title":"182. Conjugated\nMacrocycles. Part XXXII. Absorption\nSpectra of Tetrazaporphins and Phthalocyanines. Formation of Pyridine\nSalts","volume":"0","author":"Whalley","year":"1961","journal-title":"J. Chem. Soc."},{"key":"2026090114382196700_cit135","doi-asserted-by":"publisher","first-page":"2143","DOI":"10.1002\/chin.197806293","article-title":"Tert-butyl\nderivatives of porphyrazine","volume":"47","author":"Kopranenkov","year":"1977","journal-title":"Zh. Obshch. Khim."},{"key":"2026090114382196700_cit136","doi-asserted-by":"publisher","first-page":"4839","DOI":"10.1039\/JR9520004839","article-title":"944. Conjugated Macrocylces. Part\nXXII. Tetrazaporphin and Its Metallic Derivatives","author":"Linstead","year":"1952","journal-title":"J. Chem. Soc."},{"key":"2026090114382196700_cit137","unstructured":"Eda, T.\n          \n          Naphthalocyanine\nCompounds. US4622179A, November 11\n          1986\n          https:\/\/patents.google.com\/patent\/US4622179A\/en (accessed 2024\u201303\u201318)."},{"key":"2026090114382196700_cit138","doi-asserted-by":"publisher","first-page":"765","DOI":"10.1021\/ja411016f","article-title":"Design, Synthesis,\nand Properties of Phthalocyanine Complexes with Main-Group Elements\nShowing Main Absorption and Fluorescence beyond 1000 Nm","volume":"136","author":"Furuyama","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114382196700_cit139","doi-asserted-by":"publisher","first-page":"2313","DOI":"10.1002\/chin.198119308","article-title":"Phthalocyanines and\nrelated compounds. XVIII. Phenoxy- and phenylthio-substituted phthalocyanines","volume":"50","author":"Derkacheva","year":"1980","journal-title":"Zh. Obshch. Khim."},{"key":"2026090114382196700_cit140","doi-asserted-by":"publisher","first-page":"1636","DOI":"10.1021\/ic00111a004","article-title":"Regiospecific\nand Nonlinear Substituent Effects on the Electronic and Fluorescence\nSpectra of Phthalocyanines","volume":"34","author":"Kobayashi","year":"1995","journal-title":"Inorg. Chem."},{"key":"2026090114382196700_cit141","doi-asserted-by":"publisher","first-page":"15655","DOI":"10.1021\/acs.jmedchem.0c01072","article-title":"Novel Targeted Photosensitizer as\nan Immunomodulator for Highly Efficient Therapy of T-Cell Acute Lymphoblastic\nLeukemia","volume":"63","author":"Yuan","year":"2020","journal-title":"J. Med. Chem."},{"key":"2026090114382196700_cit142","doi-asserted-by":"publisher","first-page":"4225","DOI":"10.1002\/chem.201103516","article-title":"A Phthalocyanine-Peptide Conjugate\nwith High in vitro\nPhotodynamic Activity and Enhanced in vivo Tumor-Retention Property","volume":"18","author":"Ke","year":"2012","journal-title":"Chem.\u2500Eur. J."},{"key":"2026090114382196700_cit143","doi-asserted-by":"publisher","first-page":"307","DOI":"10.1139\/v96-035","article-title":"The use of bisphthalonitriles in\nthe synthesis of side-strapped 1,11,15,25-tetrasubstituted phthalocyanines","volume":"74","author":"Leznoff","year":"1996","journal-title":"Can. J. Chem."},{"key":"2026090114382196700_cit144","doi-asserted-by":"publisher","first-page":"3234","DOI":"10.1021\/acs.orglett.6b01489","article-title":"Synthesis of an ABCD-Type Phthalocyanine\nby Intramolecular Cyclization Reaction","volume":"18","author":"Chow","year":"2016","journal-title":"Org.\nLett."},{"key":"2026090114382196700_cit145","doi-asserted-by":"publisher","first-page":"14306","DOI":"10.1021\/acs.joc.9b02126","article-title":"Chemoselective\nSynthesis of Aryloxy-Substituted Phthalocyanines","volume":"84","author":"Furuyama","year":"2019","journal-title":"J. Org. Chem."}],"container-title":["The Journal of Physical\nChemistry A"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jpca.6c02666","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article-pdf\/130\/34\/6707\/66556221\/acs.jpca.6c02666.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article-pdf\/130\/34\/6707\/66556221\/acs.jpca.6c02666.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T18:38:36Z","timestamp":1788287916000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article\/130\/34\/6707\/5256110\/From-the-Four-Orbital-Model-to-the-Three-Orbital"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,14]]},"references-count":145,"journal-issue":{"issue":"34","published-online":{"date-parts":[[2026,8,14]]},"published-print":{"date-parts":[[2026,8,27]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jpca.6c02666","relation":{},"ISSN":["1089-5639","1520-5215"],"issn-type":[{"value":"1089-5639","type":"print"},{"value":"1520-5215","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,14]]}}}