{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T14:52:59Z","timestamp":1791298379983,"version":"4.1.0"},"reference-count":135,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2006,10,16]],"date-time":"2006-10-16T00:00:00Z","timestamp":1160956800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2007,1,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The synthesis, structures, and optical and electrochemical properties of <jats:italic>meso<\/jats:italic>\u2010phosphorylporphyrins are described. The copper\u2010catalyzed carbon\u2013phosphorus cross\u2010coupling reaction of a <jats:italic>meso<\/jats:italic>\u2010iodoporphyrin with di\u2010<jats:italic>n<\/jats:italic>\u2010butyl phosphite and diphenylphosphane oxide has proved to be an efficient and general method for the synthesis of <jats:italic>meso<\/jats:italic>\u2010phosphorylporphyrins. Zinc phosphorylporphyrins thus obtained readily undergo self\u2010organization through P\u2013oxo\u2013Zn coordination to form noncovalently linked, cofacial porphyrin dimers or linear oligomers, which have been characterized by spectroscopic methods and X\u2010ray crystallographic analyses. In toluene, CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>, and CHCl<jats:sub>3<\/jats:sub>, the zinc phosphorylporphyrins exist mostly as dimers or monomers, depending on their concentrations, the temperature, and the presence of additives. The self\u2010association constants for dimerization in toluene have been determined by UV\/Vis absorption titration measurements. The <jats:italic>meso<\/jats:italic>\u2010diphenylphosphorylporphyrin dimer displays excitonic coupling of the Soret band with a splitting energy of 940\u2005cm<jats:sup>\u22121<\/jats:sup>. Fluorescence lifetimes of the zinc phosphorylporphyrins have been found to be affected only slightly by the concentration of the solution, and by the addition of triphenylphosphane oxide, suggesting that the effect of dimerization on their photodynamics in the S<jats:sub>1<\/jats:sub> state is negligible. On the other hand, the effect of dimerization is clearly reflected in their electrochemical oxidation processes, as the initially produced radical cations are efficiently delocalized over the two porphyrin rings. These findings demonstrate the potential utility of <jats:italic>meso<\/jats:italic>\u2010phosphorylporphyrins as new models for the special pair in photosynthesis and as new building blocks for porphyrin\u2010based supramolecular materials.<\/jats:p>","DOI":"10.1002\/chem.200600835","type":"journal-article","created":{"date-parts":[[2006,10,17]],"date-time":"2006-10-17T02:05:16Z","timestamp":1161050716000},"page":"891-901","source":"Crossref","is-referenced-by-count":74,"title":["Synthesis, Structures, and Properties of <i>meso<\/i>\u2010Phosphorylporphyrins: Self\u2010Organization through P\u2013Oxo\u2013Zinc Coordination"],"prefix":"10.1002","volume":"13","author":[{"given":"Yoshihiro","family":"Matano","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazuaki","family":"Matsumoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yukiko","family":"Terasaka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroki","family":"Hotta","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasuyuki","family":"Araki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Osamu","family":"Ito","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Motoo","family":"Shiro","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takahiro","family":"Sasamori","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Norihiro","family":"Tokitoh","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroshi","family":"Imahori","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2007,1,4]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","first-page":"131","volume-title":"Comprehensive Supramolecular Chemistry Vol.\u20059","author":"Sanders J. K. M.","year":"1996"},{"key":"e_1_2_6_3_2","first-page":"687","volume-title":"Comprehensive Supramolecular Chemistry Vol.\u200510","author":"Balzani V.","year":"1996"},{"key":"e_1_2_6_4_2","first-page":"347","volume-title":"The Porphyrin Handbook Vol.\u20053","author":"Sanders J. K. M.","year":"2000"},{"key":"e_1_2_6_5_2","first-page":"1","volume-title":"The Porphyrin Handbook Vol.\u20056","author":"Chambron J.\u2010C.","year":"2000"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(99)00211-8"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(99)00207-6"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0898-8838(02)53006-3"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200300094"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-08-092392-5.50008-0"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1142\/S1088424604000155"},{"key":"e_1_2_6_12_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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recently Arnold and co\u2010workers independently reported the synthesis ofmeso\u2010phosphorylporphyrins based on the Pd\u2010catalyzed C\uf8ffP cross\u2010coupling reaction. See:"},{"key":"e_1_2_6_93_2","doi-asserted-by":"publisher","DOI":"10.1142\/S1088424606000211"},{"key":"e_1_2_6_94_2","author":"Atefi F.","journal-title":"Inorg. Chem."},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990356j"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0346640"},{"key":"e_1_2_6_97_2","unstructured":"The chemical shifts of the peripheral protons remain almost identical from \u221210\u2009\u00b0C to \u221250\u2009\u00b0C for2\u2009Znand from 20\u2009\u00b0C to \u221260\u2009\u00b0C for3\u2009Zn implying that these compounds exist mostly as dimers in these temperature ranges."},{"key":"e_1_2_6_98_2","unstructured":"It is well known that themeso\u2010phenyl rings of TPP\u2010type porphyrins do not lie in the same plane as the porphyrin ring due to steric repulsion with the neighboring \u03b2\u2010protons."},{"key":"e_1_2_6_99_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0277-5387(00)83241-6"},{"key":"e_1_2_6_100_2","unstructured":"X\u2010ray crystal structure data for (2\u2009Zn)2: formula C140H178N8O6P2Zn2 triclinic crystal size 0.20\u00d70.10\u00d70.05\u2005mm space groupP$\\bar 1$ a= 10.5923(14) b= 17.761(2) c= 18.720(2)\u2005\u00c5 \u03b1= 86.268(8) \u03b2= 80.937(8) \u03b3= 74.127(8)\u00b0 V= 3344.3(7)\u2005\u00c53 Z= 1 \u03c1calcd= 1.123\u2005g\u2009cm\u22123 2\u03b8max= 136.4\u00b0 T= 93.1\u2005K \u03bc= 1.084\u2005mm\u22121 Tmin= 0.947 Tmax= 0.736 35\u2009256 measured reflections 11\u2009909 independent reflections (Rint= 0.081) 714 refined parameters wR2= 0.3378 R= 0.1122 [I>2.00\u03c3(I)] GOF = 1.093 max\/min residual electron density 2.21\/\u22120.98\u2005e\u2009\u00c5\u22123. CCDC\u2010281481 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_6_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00138a051"},{"key":"e_1_2_6_102_2","unstructured":"Zn\u2013O 1.896(3)\u20131.910(3)\u2005\u00c5; P\uf8feO 1.493(3)\u20131.507(3)\u2005\u00c5; P\u2010O\u2010Zn 147.1(2)\u2013170.1(2)\u00b0. See ref.\u2005[19]."},{"key":"e_1_2_6_103_2","unstructured":"\u00a0"},{"key":"e_1_2_6_104_2","doi-asserted-by":"publisher","DOI":"10.1039\/j19700002778"},{"key":"e_1_2_6_105_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108270192006176"},{"key":"e_1_2_6_106_2","doi-asserted-by":"publisher","DOI":"10.1038\/35082000"},{"key":"e_1_2_6_107_2","volume-title":"The Photosynthetic Reaction Center, Vol.\u20052","year":"1993"},{"key":"e_1_2_6_108_2","unstructured":"X\u2010ray crystal structure data for3\u2009Zn: formula C74H81N4OPZn\u22c50.5\u2009H2O monoclinic crystal size 0.15\u00d70.07\u00d70.02\u2005mm space groupP21\/n(no.\u200514) a= 18.9921(4) b= 9.8546(2) c= 36.1694(9)\u2005\u00c5 \u03b2= 95.8864(8)\u00b0 V= 6733.8(3)\u2005\u00c53 Z= 4 \u03c1calcd= 1.132\u2005g\u2009cm\u22123 2\u03b8max= 50.0\u00b0 T= 103\u2005K \u03bc= 0.434\u2005mm\u22121 Tmin= 0.9378 Tmax= 0.9914 53\u2009301 measured reflections 11\u2009856 independent reflections (Rint= 0.1614) 745 refined parameters wR2= 0.1648 R= 0.0858 [I>2.00\u03c3(I)] GOF = 1.081 max\/min residual electron density 0.581\/\u22120.395\u2005e\u2009\u00c5\u22123. CCDC\u2010609799 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_6_109_2","unstructured":"\u00a0"},{"key":"e_1_2_6_110_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39950002567"},{"key":"e_1_2_6_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic970884w"},{"key":"e_1_2_6_112_2","doi-asserted-by":"publisher","DOI":"10.1039\/b101033f"},{"key":"e_1_2_6_113_2","unstructured":"All attempts to grow single crystals of3\u2009Znfrom hexane\/CHCl3were unsuccessful."},{"key":"e_1_2_6_114_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac196511030371"},{"key":"e_1_2_6_115_2","unstructured":"For discussion about the excitonic coupling of covalently and noncovalently linked porphyrin dimers see:"},{"key":"e_1_2_6_116_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00365a085"},{"key":"e_1_2_6_117_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00221a079"},{"key":"e_1_2_6_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00011a024"},{"key":"e_1_2_6_119_2","unstructured":"The absorption spectra with energies given in cm\u22121 were deconvoluted into three Gaussian bands and analyzed."},{"key":"e_1_2_6_120_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00043a016"},{"key":"e_1_2_6_121_2","unstructured":"For instance theKavalue of6was reported to be \u22481011\u2009M\u22121in CHCl3at 25\u2009\u00b0C. See ref.\u2005[3\u2009f]."},{"key":"e_1_2_6_122_2","unstructured":"The [monomer]\/[dimer] ratios at these concentrations are estimated to be 61:39 to 99:1 for2\u2009Znand 18:82 to 91:9 for3\u2009Zn respectively based on theKavalues in Equation\u2005(1)."},{"key":"e_1_2_6_123_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00031a028"},{"key":"e_1_2_6_124_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9624376"},{"key":"e_1_2_6_125_2","doi-asserted-by":"crossref","unstructured":"M.\u2005C. Burla M. Camalli B. Carrozzini G.\u2005L. Cascarano C. Giacovazzo G. Polidori R. Spagna SIR2002 J. Appl. Crystallogr.2003 36 1103.","DOI":"10.1107\/S0021889803012585"},{"key":"e_1_2_6_126_2","unstructured":"P.\u2005T. Beurskens G. Admiraal G. Beurskens W.\u2005P. Bosman R. de\u2005Gelder R. Israel J.\u2005M.\u2005M. Smits The DIRDIF\u201099 Program System Technical Report of the Crystallography Laboratory University of Nijmegen (The Netherlands) 1999."},{"key":"e_1_2_6_127_2","unstructured":"Crystal Structure\u20053.7.0 Crystal Structure Analysis Package Rigaku and Rigaku\/MSC 9009 New Trails Drive The Woodlands TX 77381 (USA) 2000\u20132004."},{"key":"e_1_2_6_128_2","unstructured":"D.\u2005J. Watkin C.\u2005K. Prout J.\u2005R. Carruthers P.\u2005W. Betteridge Crystals Issue 10 Chemical Crystallography Laboratory Oxford (UK) 1996."},{"key":"e_1_2_6_129_2","unstructured":"G.\u2005M. Sheldrick SHELX97 University of G\u00f6ttingen (Germany) 1997."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200600835","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200600835","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:15:56Z","timestamp":1760274956000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200600835"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,1,4]]},"references-count":135,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2007,1,12]]}},"alternative-id":["10.1002\/chem.200600835"],"URL":"https:\/\/doi.org\/10.1002\/chem.200600835","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2007,1,4]]}}}