{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T14:53:01Z","timestamp":1791298381898,"version":"4.1.0"},"reference-count":132,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2007,9,24]],"date-time":"2007-09-24T00:00:00Z","timestamp":1190592000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2007,11,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The synthesis and aggregation behavior of <jats:italic>meso<\/jats:italic>\u2010sulfinylporphyrins are described. The copper\u2010catalyzed C\u2013S cross\u2010coupling reaction of a <jats:italic>meso<\/jats:italic>\u2010iodoporphyrin with benzenethiol and <jats:italic>n<\/jats:italic>\u2010octanethiol has proved to be an efficient method for the synthesis of <jats:italic>meso<\/jats:italic>\u2010sulfanylporphyrins, which are oxygenated by <jats:italic>m<\/jats:italic>\u2010chloroperbenzoic acid to produce the corresponding <jats:italic>meso<\/jats:italic>\u2010sulfinylporphyrins. Optically active zinc <jats:italic>meso<\/jats:italic>\u2010sulfinylporphyrins were successfully isolated by means of optical resolution of the racemates on a chiral HPLC column. Zinc sulfinylporphyrins readily undergo self\u2010organization through S\u2013oxo\u2013zinc coordination to form cofacial porphyrin dimers in solution, in which the hetero\u2010 and homodimers are present as a diastereomeric mixture. The aggregation modes of the S\u2013oxo\u2010tethered porphyrin dimers were fully characterized by <jats:sup>1<\/jats:sup>H\u2005NMR, IR, and UV\/Vis spectroscopy as well as DFT calculations on their model compounds, thus revealing that the self\u2010aggregation behavior depends on the combination of S chirality. The absolute configurations at the sulfur center can be determined by the exciton\u2010coupled CD method. The observed self\u2010association constant for the S\u2013oxo\u2010tethered dimerization of (<jats:italic>S<\/jats:italic>)\u2010phenylsulfinylporphyrin in toluene is larger than that in dichloromethane, which reflects the difference in dipole moments between the homodimer and the monomer. In cyclic and differential pulse voltammetry, the first oxidation process of the cofacial dimers is split into two reversible steps, which indicates that the initially produced \u03c0 radical cations are delocalized efficiently between the two porphyrin rings. The present findings demonstrate the potential utility of <jats:italic>meso<\/jats:italic>\u2010sulfinyl groups as promising ligands for investigating the effects of peripheral chirality on the structures and optical and electrochemical properties of metal\u2010assisted porphyrin self\u2010assemblies.<\/jats:p>","DOI":"10.1002\/asia.200700191","type":"journal-article","created":{"date-parts":[[2007,9,24]],"date-time":"2007-09-24T11:46:42Z","timestamp":1190634402000},"page":"1417-1429","source":"Crossref","is-referenced-by-count":25,"title":["Synthesis and Aggregation Behavior of <i>meso<\/i>\u2010Sulfinylporphyrins: Evaluation of S\u2010Chirality Effects on the Self\u2010Organization to S\u2013Oxo\u2010Tethered Cofacial Porphyrin Dimers"],"prefix":"10.1002","volume":"2","author":[{"given":"Yoshihiro","family":"Matano","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomonori","family":"Shinokura","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazuaki","family":"Matsumoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroshi","family":"Imahori","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haruyuki","family":"Nakano","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2007,10,26]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2836(84)80011-X"},{"key":"e_1_2_6_3_2","volume-title":"The Photosynthetic Reaction Center","year":"1993"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","first-page":"131","volume-title":"Comprehensive Supramolecular Chemistry, Vol.\u20059","author":"Sanders J. K. M.","year":"1996"},{"key":"e_1_2_6_6_2","first-page":"687","volume-title":"Comprehensive Supramolecular Chemistry, Vol.\u200510","author":"Balzani V.","year":"1996"},{"key":"e_1_2_6_7_2","first-page":"347","volume-title":"The Porphyrin Handbook, Vol.\u20053","author":"Sanders J. K. M.","year":"2000"},{"key":"e_1_2_6_8_2","first-page":"1","volume-title":"The Porphyrin Handbook, Vol.\u20056","author":"Chambron J.\u2010C.","year":"2000"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(99)00211-8"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(99)00207-6"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0898-8838(02)53006-3"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200300094"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-08-092392-5.50008-0"},{"key":"e_1_2_6_14_2","first-page":"156","volume-title":"J. Porphyrins Phthalocyanines","author":"Kobuke Y.","year":"2004"},{"key":"e_1_2_6_15_2","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1007\/b98166","volume":"245","author":"Drain C. M.","year":"2005","journal-title":"Top. Curr. 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see:"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(93)85122-D"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980904)110:17<2537::AID-ANGE2537>3.0.CO;2-3"},{"key":"e_1_2_6_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980918)37:17<2368::AID-ANIE2368>3.0.CO;2-K"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1039\/a807876i"},{"key":"e_1_2_6_49_2","unstructured":"For examples see:"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200250465"},{"key":"e_1_2_6_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200250465"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)01128-1"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200400151"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400664"},{"key":"e_1_2_6_54_2","unstructured":"For examples see:"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/1011-1344(92)85141-G"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39950001925"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1997.487"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0928-4931(99)00098-3"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1520-636X(2000)12:4<237::AID-CHIR10>3.0.CO;2-6"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.1039"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20020603)8:11<2476::AID-CHEM2476>3.0.CO;2-E"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(02)00166-7"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1023\/A:1014951513848"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462762"},{"key":"e_1_2_6_64_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462762"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500909"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0584469"},{"key":"e_1_2_6_67_2","unstructured":"\u00a0"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1142\/S1088424606000211"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic060372u"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1039\/b703589f"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200600835"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00006a019"},{"key":"e_1_2_6_73_2","unstructured":"\u00a0"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(20000317)112:6<1108::AID-ANGE1108>3.0.CO;2-#"},{"key":"e_1_2_6_74_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(20000317)39:6<1066::AID-ANIE1066>3.0.CO;2-G"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo026610u"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic034559m"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200490288"},{"key":"e_1_2_6_78_2","unstructured":"\u00a0"},{"key":"e_1_2_6_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol035081t"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.05.089"},{"key":"e_1_2_6_81_2","unstructured":"\u00a0"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)02303-0"},{"key":"e_1_2_6_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0108641"},{"key":"e_1_2_6_84_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)01837-9"},{"key":"e_1_2_6_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo034063m"},{"key":"e_1_2_6_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049440b"},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo048552d"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0618728"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990356j"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0264105"},{"key":"e_1_2_6_91_2","doi-asserted-by":"publisher","DOI":"10.1142\/S1088424602000816"},{"key":"e_1_2_6_92_2","unstructured":"In CD2Cl2 the signals of the 3 7\u2010\u03b2 protons of4H2and5H2coalesced at \u221215 and 25\u2009\u00b0C respectively."},{"key":"e_1_2_6_93_2","unstructured":"The nonequivalence of all the \u03b2 protons is not due to the S chirality itself because such discrimination was not observed for4H2and5H2."},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2004.02.005"},{"key":"e_1_2_6_95_2","unstructured":"If the aggregates consist ofnpieces (n\u22653) of sulfinylporphyrins more than one pair of S\u2013oxo\u2010linked diastereomers can be formed. The spectra shown in Figures\u20051\u2009b and 2\u2009b imply that the contribution of cyclic linear or branched higher oligomers is negligible in solution."},{"key":"e_1_2_6_96_2","unstructured":"It is well\u2010known that themeso\u2010phenyl rings of tetraphenylporphyrin are not on the same plane of the porphyrin ring due to steric repulsion with neighboring \u03b2 protons."},{"key":"e_1_2_6_97_2","doi-asserted-by":"publisher","DOI":"10.1038\/35082000"},{"key":"e_1_2_6_98_2","unstructured":"For examples see:"},{"key":"e_1_2_6_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00131a033"},{"key":"e_1_2_6_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja960126p"},{"key":"e_1_2_6_101_2","first-page":"361","volume-title":"Circular Dichroism: Principles and Applications","author":"Nakanishi K.","year":"1994"},{"key":"e_1_2_6_102_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00221-X"},{"key":"e_1_2_6_103_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20011105)113:21<4216::AID-ANGE4216>3.0.CO;2-N"},{"key":"e_1_2_6_103_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20011105)40:21<4092::AID-ANIE4092>3.0.CO;2-R"},{"key":"e_1_2_6_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma051884f"},{"key":"e_1_2_6_105_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac196511030371"},{"key":"e_1_2_6_106_2","unstructured":"For discussions on the excitonic coupling of covalently and noncovalently linked porphyrin dimers see:"},{"key":"e_1_2_6_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00365a085"},{"key":"e_1_2_6_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00221a079"},{"key":"e_1_2_6_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00011a024"},{"key":"e_1_2_6_110_2","unstructured":"The absorption spectra in which energies are given in cm\u22121 were deconvoluted into three Gaussian bands and analyzed by ORIGIN."},{"key":"e_1_2_6_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00032a005"},{"key":"e_1_2_6_112_2","unstructured":"For instance theKavalue of9was reported to be about 1011\u2009M\u22121in CHCl3at 25\u2009\u00b0C; see reference\u2005[4]."},{"key":"e_1_2_6_113_2","unstructured":"This value is close to the association constant of (S)\u20104Zn\u2013OSPh2adduct (49\u2009M\u22121in toluene at 25\u2009\u00b0C) determined by competitive titration; see Experimental Section."},{"key":"e_1_2_6_114_2","unstructured":"In the electrochemical measurements the racemates of4Znand5Znwere used. Thus the voltammograms depicted in Figure\u20058 andFigure\u2005S14 of the Supporting Informationare superimpositions of those of the homo\u2010 and heterodimers although the differences in their oxidation potentials are considered to be very small."},{"key":"e_1_2_6_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00031a028"},{"key":"e_1_2_6_116_2","unstructured":"The Schugar dimer8showed four separate one\u2010electron oxidation potentials at +0.56 +1.01 +1.21 and +1.55\u2005V (vs. saturated calomel electrode (SCE); in CH2Cl2containingnBu4NBF4) [3f]and the Kobuke dimer9revealed oxidation potentials at +0.414 +0.632 +0.968 and +1.120\u2005V (vs. Ag\/Ag+; in CHCl3containing TBAP).[4f]The oxidation potentials of4Znand5Znversus SCE were calculated to be +0.77 +1.02 +1.20\u2005V and +0.75 +1.01 +1.19\u2005V respectively."},{"key":"e_1_2_6_117_2","unstructured":"R.\u2005A. Binstead A.\u2005D. Zuberb\u00fchler SPECFIT Global Analysis System\u20052.10 (Rev.\u2005X) Spectrum Software Associates Chapel Hill NC (USA) 1998."},{"key":"e_1_2_6_118_2","unstructured":"\u00a0"},{"key":"e_1_2_6_119_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.438955"},{"key":"e_1_2_6_120_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.438980"},{"key":"e_1_2_6_121_2","unstructured":"\u00a0"},{"key":"e_1_2_6_122_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_2_6_123_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.37.785"},{"key":"e_1_2_6_124_2","unstructured":"M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman J.\u2005A. Montgomery \u2005Jr. T. Vreven K.\u2005N. Kudin J.\u2005C. Burant J.\u2005M. Millam S.\u2005S. Iyengar J. Tomasi V. Barone B. Mennucci M. Cossi G. Scalmani N. Rega G.\u2005A. Petersson H. Nakatsuji M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai M. Klene X. Li J.\u2005E. Knox H.\u2005P. Hratchian J.\u2005B. Cross C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski P.\u2005Y. Ayala K. Morokuma G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg V.\u2005G. Zakrzewski S. Dapprich A.\u2005D. Daniels M.\u2005C. Strain O. Farkas D.\u2005K. Malick A.\u2005D. Rabuck K. Raghavachari J.\u2005B. Foresman J.\u2005V. Ortiz Q. Cui A.\u2005G. Baboul S. Clifford J. Cioslowski B.\u2005B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R.\u2005L. Martin D.\u2005J. Fox T. Keith M.\u2005A. Al\u2010Laham C.\u2005Y. Peng A. Nanayakkara M. Challacombe P.\u2005M.\u2005W. Gill B. Johnson W. Chen M.\u2005W. Wong C. Gonzalez J.\u2005A. Pople Gaussian\u200503 Gaussian Inc. 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