{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,9]],"date-time":"2026-03-09T10:47:48Z","timestamp":1773053268041,"version":"3.50.1"},"reference-count":87,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2023,7,17]],"date-time":"2023-07-17T00:00:00Z","timestamp":1689552000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"JSPS KAKENHI","doi-asserted-by":"publisher","award":["JP21K14615"],"award-info":[{"award-number":["JP21K14615"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"JSPS KAKENHI","doi-asserted-by":"publisher","award":["JP22K05070"],"award-info":[{"award-number":["JP22K05070"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Sulfur-containing macrocycles have attracted substantial interest because they exhibit unique characteristics due to their polygonal ring-shaped skeleton. In this study, a thianthrene-based cyclic tetramer with the sulfur linker, thiacalix[4]-2,8-thianthrene (TC[4]TT), was successfully prepared from a cyclo-p-phenylenesulfide derivative using acid-induced intramolecular condensation. Single crystal X-ray diffraction revealed that TC[4]TT adopts an alternative octagonal form recessed to the inner side. Its internal cavity included small solvents, such as chloroform and carbon disulfide. Due to its polygonal geometry, TC[4]TT laminated in a honeycomb-like pattern with a porous channel. Furthermore, TC[4]TT showed fluorescence and phosphorescence emission in a CH2Cl2 solution at ambient and liquid nitrogen temperatures. Both emission bands were slightly redshifted compared with those of the reference compounds (di(thanthren-2-yl)sulfane (TT2S) and thianthrene (TT)). This work describes a sulfur-containing thiacalixheterocycle-based macrocyclic system with intriguing supramolecular chemistry based on molecular tiling and photophysical properties in solution.<\/jats:p>","DOI":"10.3390\/molecules28145462","type":"journal-article","created":{"date-parts":[[2023,7,18]],"date-time":"2023-07-18T01:46:02Z","timestamp":1689644762000},"page":"5462","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis, Structure, and Characterization of Thiacalix[4]-2,8-thianthrene"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0378-7366","authenticated-orcid":false,"given":"Masafumi","family":"Ueda","sequence":"first","affiliation":[{"name":"Department of Chemistry, Graduate School of Science, Kitasato University, Sagamihara 252-0373, Kanagawa, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Moe","family":"Isozaki","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Science, Kitasato University, Sagamihara 252-0373, Kanagawa, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yasuhiro","family":"Mazaki","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Science, Kitasato University, Sagamihara 252-0373, Kanagawa, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,7,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1675","DOI":"10.1002\/ejoc.200300492","article-title":"Chemistry of Thiacalixarenes","volume":"2004","year":"2004","journal-title":"Eur. J. Org. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"5291","DOI":"10.1021\/cr050565j","article-title":"Thiacalixarenes","volume":"106","author":"Morohashi","year":"2006","journal-title":"Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"646","DOI":"10.1016\/j.dyepig.2007.09.005","article-title":"The synthesis and complexation of novel azosubstituted calix[4]arenes and thiacalix[4]arenes","volume":"77","author":"Lang","year":"2008","journal-title":"Dye. Pigment."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2057","DOI":"10.1016\/j.tet.2007.12.048","article-title":"Design, synthesis, characterization, and preliminary complexation studies of chromogenic vanadophiles: 1,3-alternate thiacalix[4]arene tetrahydroxyamic acids","volume":"64","author":"Patel","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"985","DOI":"10.1016\/j.msec.2007.10.037","article-title":"Thiacalix[4]arene derivatives as extractants for metal ions in aqueous solutions: Application to the selective facilitated transport of Ag(I)","volume":"28","author":"Zaghbani","year":"2008","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"7112","DOI":"10.1016\/j.tet.2008.05.057","article-title":"The synthesis of p-tert-butyl thiacalix[4]arene functionalized with secondary amide groups at the lower rim and their extraction properties and self-assembly into nanoscale aggregates","volume":"64","author":"Stoikov","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"7489","DOI":"10.1016\/j.tet.2008.05.102","article-title":"Solvent extraction and self-assembly of nanosized aggregates of p-tert-butyl thiacalix[4]arenes tetrasubstituted at the lower rim by tertiary amide groups and monocharged metal cations in the organic phase","volume":"64","author":"Stoikov","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_8","first-page":"15838","article-title":"Self-Assembly of Stereoisomers of p-tert-Butyl Thiacalix[4]arenes Tetrasubstituted at the Lower Rim by a Tertiary Amide Group with Cations of p- and d-Elements in the Organic Phase","volume":"113","author":"Stoikov","year":"2009","journal-title":"J. Phys. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1621","DOI":"10.1134\/S0036023612120212","article-title":"Extraction of Palladium with Thiacalix[4]arenes from Nitric Acid Nitrate\u2013Nitrite Solution","volume":"57","author":"Torgov","year":"2012","journal-title":"Russ. J. Inorg. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2559","DOI":"10.1021\/ie404161s","article-title":"Synthesis and Characterization of Dimethylthiocarbomoyl-Modified Thiacalix[n]arenes for Selective Pd(II)-Ion Extraction","volume":"53","author":"Gandhi","year":"2014","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1016\/j.micromeso.2010.01.018","article-title":"Molecular transport in thiacalix[4]arene-modified nanoporous colloidal films","volume":"131","author":"Mollard","year":"2010","journal-title":"Macroporous Mesoporous Mater."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"7006","DOI":"10.1002\/chem.200700354","article-title":"Oxovanadium(V) tetrathiacalix[4]arene Complexes and Their Activity as Oxidation Catalyst","volume":"13","author":"Hoppe","year":"2007","journal-title":"Chem. Eur. J."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"5126","DOI":"10.1039\/b712351e","article-title":"Molecular tectonics: On the formation of 1-D silver coordination networks by thiacalixarenes bearing nitrile groups","volume":"44","author":"Kozlova","year":"2007","journal-title":"Dalton Trans."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1038","DOI":"10.1021\/cg0700014","article-title":"A Novel Supramolecular Assembly Constructed by Cu\/imidazole Complex with 1,2-Alternate p-Sulfonatothiacalix[4]arene","volume":"7","author":"Guo","year":"2007","journal-title":"Cryst. Growth Des."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2601","DOI":"10.1021\/cg070607s","article-title":"Comparable Inclusion and Aggregation Structures of p-Sulfonatothiacalix[4]arene and p-Sulfonatocalix[4]arene upon Complexation with Quinoline Guests","volume":"7","author":"Liu","year":"2007","journal-title":"Cryst. Growth Des."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2514","DOI":"10.1039\/b902267h","article-title":"Molecular tectonics: 3-D organisation of decanuclear silver nanoclusters","volume":"18","author":"Kozlova","year":"2009","journal-title":"Chem. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4989","DOI":"10.1002\/ejic.200900699","article-title":"Self-Assembly from Two-Dimensional Layered Networks to Tetranuclear Structures: Syntheses, Structures, and Properties of Four Copper\u2013Thiacalix[[4]arene Compounds","volume":"2009","author":"Bi","year":"2009","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1311","DOI":"10.1039\/B916317D","article-title":"Thiacalix[4]arene\u2013rubidium assembly: Supramolecular architecture based on alkali metal coordination and cation-\u03c0 interactions","volume":"12","author":"Yamada","year":"2010","journal-title":"CrystEngComm"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5598","DOI":"10.1021\/ja101598p","article-title":"Chiral Kagome Network from Thiacalix[4]arene Tetrasulfonate at the Interface of Aqueous Solution\/Au(111) Surface: An in Situ Electrochemical Scanning Tunneling Microscopy Study","volume":"132","author":"Chen","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"6920","DOI":"10.1039\/c1ce05813d","article-title":"Channel structure for guest inclusion based on hexametric assembly of thiacalix[4]arene analogue","volume":"13","author":"Hamada","year":"2011","journal-title":"CrystEngComm"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1039\/C0CE00129E","article-title":"Pendant orientation and its influence on the formation of hydrogen-bonded thiacalixarene nanotubes","volume":"13","author":"Yang","year":"2011","journal-title":"CrystEngComm"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2494","DOI":"10.1039\/c0ce00824a","article-title":"Thiacalix[4]arene  potassium assemblies: A supramolecular architecture based on coordination polymers and a dimeric structure based on triangular pyramidal arrangements","volume":"13","author":"Yamada","year":"2011","journal-title":"CrystEngComm"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7392","DOI":"10.1016\/j.tet.2011.07.027","article-title":"Thiacalix[4]arene\u2013alkali metal assemblies: Crystal structures and guest-binding capabilities of supramolecular architectures supported by metal coordination and cation\u2013\u03c0 interactions","volume":"67","author":"Yamada","year":"2011","journal-title":"Tetrahedron"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"14053","DOI":"10.1021\/la202536x","article-title":"Cascade and Commutative Self-Assembles of Nanoscale Three-Component Systems Controlled by the Conformation of Thiacalix[4]arene","volume":"27","author":"Yushkova","year":"2011","journal-title":"Langmuir"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1177","DOI":"10.1002\/poc.2981","article-title":"Slef-assembly of p-tert-butyl thiacalix[4]arenes and metal cations into nanoscale three-dimensional particles","volume":"25","author":"Stoikov","year":"2012","journal-title":"J. Phys. Org. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"3556","DOI":"10.1039\/C3RA44052D","article-title":"Supramolecular \u201ccontainers\u201d: Self-assembly and functionalization of thiacalix[4]arenes for recognition of amino-and dicarboxylic acids","volume":"4","author":"Andreyko","year":"2014","journal-title":"RSC Adv."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"7663","DOI":"10.1039\/C5CE01088H","article-title":"\u2018Honeycomb\u2019 nanotube assembly based on thiacalix[4]arene derivatives by weak interactions","volume":"17","author":"Wang","year":"2015","journal-title":"CrystEngComm"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"356","DOI":"10.1002\/ejic.201901216","article-title":"A Thiacalix Basket and Its Anion-Dependent 2-D and 3-D Silver(I) Coordination Polymers via Exo-Coordination","volume":"2020","author":"Ju","year":"2020","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"7617","DOI":"10.1039\/D0CE01198C","article-title":"Influence of anions and mole ratio on the formation of 2-D coordination networks of thiacalix[4]-bis-monothiacrown-5","volume":"22","author":"Ju","year":"2020","journal-title":"CrystEngComm"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3271","DOI":"10.1021\/acs.cgd.2c00108","article-title":"Protein Frameworks with Thiacalixarene and Zinc","volume":"22","author":"Flood","year":"2022","journal-title":"Cryst. Growth Des."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"3906","DOI":"10.1016\/j.tetlet.2008.04.057","article-title":"Hydrophobic and metal coordination interacted architecture based on p-tert-butylthiacalix[4]arene\u2013potassium complex and its vapor absorption capability","volume":"49","author":"Yamada","year":"2008","journal-title":"Tetrahedron Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3292","DOI":"10.1021\/ol200506p","article-title":"Unique Inclusion Properties of Crystalline Powder p-tert-Butylthiacalix[4]arene toward Alcohols and Carboxylic Acids","volume":"13","author":"Morohashi","year":"2011","journal-title":"Org. Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"9008","DOI":"10.1039\/C8DT02089B","article-title":"A 2D metal-thiacalix[4]arene porous coordination polymer with 1D channels: Gas absorption\/separation and frequency response","volume":"47","author":"Geng","year":"2018","journal-title":"Dalton Trans."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"6277","DOI":"10.1021\/ic070259j","article-title":"A New Hg2+-Selective Fluorescent Sensor Based on a 1,3-Alternate Thiacalix[4]arene Anchored with Four 8-Quinolinoloxy Groups","volume":"46","author":"Praveen","year":"2007","journal-title":"Inorg. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"11153","DOI":"10.1016\/j.tet.2007.08.021","article-title":"Bifunctional fluorescent thiacalix[4]arene based chemosensor for Cu2+ and F\u2212 ions","volume":"63","author":"Bhalla","year":"2007","journal-title":"Tetrahedron"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"8095","DOI":"10.1016\/j.tet.2008.06.064","article-title":"Cu2+ and CN\u2212-selective fluorogenic sensors based on pyrene-appended thiacalix[4]arenes","volume":"64","author":"Kumar","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1039\/B816596C","article-title":"A Supramolecular sensing system for AgI t nanomolar levels by the formation of a luminescent AgI\u2013TbIII\u2013thiacalix[4]arene ternary complex","volume":"33","author":"Iki","year":"2009","journal-title":"New. J. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4340","DOI":"10.1016\/j.tet.2009.03.074","article-title":"F\u2212-Induced \u2018turn-on\u2019 fluorescent chemosensor based on 1,3-alt thiacalix[4]arene","volume":"65","author":"Kumar","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4534","DOI":"10.1002\/ejoc.200900506","article-title":"On\u2013Off Switchable Binuclear Chemosensor Based on Thiacalix[4]crown Armed with Pyrene Moieties","volume":"2009","author":"Kumar","year":"2009","journal-title":"Eur. J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"7510","DOI":"10.1016\/j.tet.2009.07.014","article-title":"Regulation of metal ion recognirion by allosteric effects in thiacalix[4]crown based receptors","volume":"65","author":"Kumar","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1045","DOI":"10.1039\/c1ra00313e","article-title":"Fluorescent probe for Fe3+ and CN\u2212 in aqueous media mimicking a memorized molecular crossword puzzle","volume":"1","author":"Kumar","year":"2011","journal-title":"RSC Adv."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3248","DOI":"10.1016\/j.tet.2011.03.008","article-title":"Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion","volume":"67","author":"Ni","year":"2011","journal-title":"Tetrahedron"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"408","DOI":"10.1039\/C1DT11169H","article-title":"Thiacalix[4]arene based fluorescent probe for sensing and imaging of Fe3+ ions","volume":"41","author":"Kumar","year":"2012","journal-title":"Dalton Trans."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1524","DOI":"10.1016\/j.tetlet.2013.01.009","article-title":"Differential fluorogenic sensing of F\u2212 versus CN\u2212 based on thiacalix[4]arene derivatives","volume":"54","author":"Kumar","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"4917","DOI":"10.1039\/C4OB00551A","article-title":"A study of allosteric binding behaviour of a 1,3-alternate thiacalix[4]arene-based receptor using fluorescence signal","volume":"12","author":"Tomiyasu","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"8521","DOI":"10.1016\/j.tet.2015.09.038","article-title":"Synthesis, crystal structure and complexation behaviour study of an efficient Cu2+ ratiometric fluorescent chemosensor based on thiacalix[4]arene","volume":"71","author":"Zhao","year":"2015","journal-title":"Tetrahedron"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"877","DOI":"10.1021\/acsomega.9b03821","article-title":"Selective Detection of Cu2+ Ions by Immobilizing Thiacalix[4]arene on Graphene Field-Effect Transistors","volume":"5","author":"Takagiri","year":"2020","journal-title":"ACS Omega"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1246\/bcsj.20140007","article-title":"Cavity-Assembled Porous Solids (CAPSs) for Nanospace-Specific Functions","volume":"87","author":"Tashiro","year":"2014","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"897","DOI":"10.1246\/cl.1997.897","article-title":"Cyclic Oligo(thio-2,5-thioenylenes)(Sulfur-bridged Calixarenes)","volume":"26","author":"Nakayama","year":"1997","journal-title":"Chem. Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2695","DOI":"10.1246\/bcsj.71.2695","article-title":"Synthesis and Structure of Sulfur-Bridged [1.n](2,5)Thiophenophanes (n = 4\u20136)","volume":"71","author":"Katano","year":"1998","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"550","DOI":"10.1016\/S1388-2481(99)00115-0","article-title":"Stereo-electrochemistry by a self assembled monolayer of sulfur-bridged calixthiophene on gold","volume":"1","author":"Nakabayashi","year":"1999","journal-title":"Electrochem. Commun."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2734","DOI":"10.1002\/anie.201410970","article-title":"Mazaki. Efficient Synthesis, Structure, and Complexation Studies of Electron-Donating Thiacalix[n]dithienothiophene","volume":"54","author":"Inoue","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1686","DOI":"10.1039\/b203540e","article-title":"Thia-calix[n]pyridines, synthesis and coordination to Cu (I,II) ions with both N and S donor atoms","volume":"16","author":"Tanaka","year":"2002","journal-title":"Chem. Commun."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1016\/S0009-2614(03)00264-1","article-title":"Laser photolysis studies on CuI complexes of thia-calix[3]pyridine. Phosphorescence from the intramolecular charge-transfer excited state","volume":"371","author":"Kinoshita","year":"2003","journal-title":"Chem. Phys. Lett."},{"key":"ref_55","first-page":"1374","article-title":"Thiacalix[3]pyridine produces a stable mononuclear rhodium(II) complex with mutual Jahn\u2013Teller effect","volume":"11","author":"Tanaka","year":"2006","journal-title":"Dalton Trans."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"452","DOI":"10.1246\/cl.2008.452","article-title":"A Thiacalix[3]pyridine Copper(I) Complex as a Highly Active Catalyst for the Olefin Aziridination Reaction","volume":"37","author":"Tsukahara","year":"2008","journal-title":"Chem. Lett."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"4161","DOI":"10.1021\/ol0617446","article-title":"Selective Synthesis of Functionalized Thia- and Oxacalix[2]arene[2]pyrimidines","volume":"8","author":"Maes","year":"2006","journal-title":"Org. Lett."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"151911","DOI":"10.1016\/j.tetlet.2020.151911","article-title":"How do fluoride ions bind to tetrathiacalix[2]arene[2]triazines?","volume":"61","author":"Pisagatti","year":"2020","journal-title":"Tetrahedron Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"10870","DOI":"10.1039\/D2RA00489E","article-title":"Synthesis and crystal structure of a sulphur-bridged molecular hoop consisting of 5,7,12,14-tetrathiapentacene","volume":"12","author":"Ueda","year":"2022","journal-title":"RSC Adv."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1016\/0379-6779(87)90832-0","article-title":"Structure and electrical conductivity of TCNQ-2,3,7,8-tetramethoxychalcogenanthracene complex","volume":"20","author":"Hinrichs","year":"1987","journal-title":"Synth. Met."},{"key":"ref_61","first-page":"259","article-title":"2,3;7,8-Bis(ethylenedioxy)thianthrene-hexafluoroarsenate [(bEDOT)AsF6]: A Mott-Hubbard Insulator Showing Evidence for Appreciable Correlation Effects","volume":"167","author":"Noreland","year":"1989","journal-title":"Mol. Cryst. Liq. Cryst."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1691","DOI":"10.1016\/0379-6779(91)91932-Z","article-title":"Structure of the organic semiconducting radical cation salt [2,3;7,8-bis(ethylenedioxy)thianthrene]hexafluoroarsenate","volume":"42","author":"Noreland","year":"1991","journal-title":"Synth. Met."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1515\/znb-2009-0201","article-title":"Thianthrene Radical Cation Hexafluorophosphate","volume":"64","author":"Beck","year":"2009","journal-title":"Z. Naturforsch. B"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2524","DOI":"10.1002\/ejic.200800895","article-title":"Synthesis and Characterization of Semiconductive Dichloridobis(thianthrene)gold(1+) tetrachloridoaurate(1\u2212)","volume":"2009","author":"Tjahjanto","year":"2009","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"6641","DOI":"10.1021\/jo00076a024","article-title":"Photoinduced Electron Transfer and Subsequent Chemical Reactions of Absorbed Thianthrene on Clay Surfaces","volume":"58","author":"Mao","year":"1993","journal-title":"J. Org. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1853","DOI":"10.1039\/C8QM00320C","article-title":"Efficient room-temperature phosphorescence based on a pure organic sulfur-containing heterocycle: Folding-induced spin-orbit coupling enhancement","volume":"2","author":"Liu","year":"2018","journal-title":"Mater. Chem. Front."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"24958","DOI":"10.1021\/acs.jpcc.8b08329","article-title":"Observation of Dual Room Temperature Fluorescence-Phosphorescence in Air, in the Crystal Form of a Thianthrene Derivative","volume":"122","author":"Pander","year":"2018","journal-title":"J. Phys. Chem. C"},{"key":"ref_68","first-page":"358","article-title":"Redox Switchable Thianthrene Cavitands","volume":"49","author":"Ong","year":"2017","journal-title":"Synthesis"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"1308","DOI":"10.1002\/ejoc.201601371","article-title":"Light- and Electricity-Driven Molecular Pushing Motor","volume":"2017","author":"Burkhart","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"5401","DOI":"10.1016\/j.tetlet.2007.06.006","article-title":"The first approach to a new family of macrocycles: Synthesis and characterization of thiacalix[2]thianthrenes","volume":"48","author":"Zieba","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1007\/s10847-011-0033-4","article-title":"Cation binding by thiacalixthianthrenes","volume":"73","author":"Thabet","year":"2012","journal-title":"J. Incl. Phenom. Macrocycl. Chem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1021\/jo01096a616","article-title":"Bromination in the Thianthrene System","volume":"23","author":"Gilman","year":"1958","journal-title":"J. Org. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"2156","DOI":"10.1021\/ja00059a009","article-title":"Power-Variable Electrophilic Trifluoromethylating Agents","volume":"115","author":"Umemoto","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"2832","DOI":"10.1002\/1521-3935(20011001)202:14<2832::AID-MACP2832>3.0.CO;2-V","article-title":"Novel Approach to Ladder-Type Polymers: Polydithiathianthrene via the Intramolecular Acid Induced Cyclization of Methylsulfinyl-Substituted Poly(meta-phenylene sulfide)","volume":"220","author":"Leuninger","year":"2001","journal-title":"Macromol. Chem. Phys."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"18443","DOI":"10.1002\/anie.202104054","article-title":"Sulphur-embedded hydrocarbon Belts: Synthesis, Structure and Redox Chemistry of Cyclothianthrenes","volume":"60","author":"Wang","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"4371","DOI":"10.1021\/jo2007253","article-title":"One-Pot Synthesis of Symmetrical and Unsymmetrical Aryl Sulfides by Pd-Catalyzed Couplings of Aryl Halides and Thioacetates","volume":"76","author":"Park","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1454","DOI":"10.1039\/D1CS00838B","article-title":"C\u2013H\u00b7\u00b7\u00b7S hydrogen bonding interactions","volume":"51","author":"Fargher","year":"2022","journal-title":"Chem. Soc. Rev."},{"key":"ref_78","unstructured":"(2019). CrysAlisPro: Data Collection and Processing Software Package, Rigaku Oxford Diffraction, Rigaku Corporatioin."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"ref_80","first-page":"3","article-title":"SHELXT\u2014Integrated space-group and crystal-structure determination","volume":"A71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."},{"key":"ref_81","first-page":"3","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."},{"key":"ref_82","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Peterson, G.A., and Nakatsuji, H. (2016). Gaussian 16, Gaussian, Inc.. Revision C.01."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1055\/s-2002-20031","article-title":"New and Facile Synthesis of Thiosulfonates from Sulfinate\/Disulfide\/I2 System","volume":"3","author":"Fujiki","year":"2002","journal-title":"Synthesis"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"4672","DOI":"10.1016\/j.tet.2011.04.057","article-title":"Synthesis of \u2018thianthrene dimer\u2019 by the coupling reaction of stannylthianthrenes in the presence of copper catalysts","volume":"67","author":"Morita","year":"2011","journal-title":"Tetrahedron"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"10923","DOI":"10.1038\/srep10923","article-title":"Understanding the Control of Singlet-Triplet Splitting for Organic Exciton Manipulating: A Combined Theoretical and Experimental Approach","volume":"5","author":"Chen","year":"2015","journal-title":"Sci. Rep."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"985","DOI":"10.1016\/j.orgel.2012.02.010","article-title":"Computational design of low singlet-triplet gap all-organic molecules for OLED application","volume":"13","author":"Gierschner","year":"2012","journal-title":"Org. Electron."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"2164","DOI":"10.1021\/jacs.0c12659","article-title":"Cyclization-Promoted Ultralong Low-Temperature Phosphorescence via Boosting Intersystem Crossing","volume":"143","author":"Zhu","year":"2021","journal-title":"J. Am. Chem. Soc."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/14\/5462\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:13:28Z","timestamp":1760127208000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/14\/5462"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,17]]},"references-count":87,"journal-issue":{"issue":"14","published-online":{"date-parts":[[2023,7]]}},"alternative-id":["molecules28145462"],"URL":"https:\/\/doi.org\/10.3390\/molecules28145462","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,17]]}}}