{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,12]],"date-time":"2026-03-12T22:58:45Z","timestamp":1773356325466,"version":"3.50.1"},"reference-count":82,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2012,1,3]],"date-time":"2012-01-03T00:00:00Z","timestamp":1325548800000},"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":[[2012,2,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The synthesis and photophysical properties of several fullerene\u2013phthalocyanine\u2013porphyrin triads (<jats:bold>1<\/jats:bold>\u2013<jats:bold>3<\/jats:bold>) and pentads (<jats:bold>4<\/jats:bold>\u2013<jats:bold>6<\/jats:bold>) are described. The three photoactive moieties were covalently connected in an one\u2010step synthesis through 1,3\u2010dipolar cycloaddition to C<jats:sub>60<\/jats:sub> of the corresponding azomethine ylides generated in\u2005situ by condensation reaction of a substituted <jats:italic>N<\/jats:italic>\u2010porphyrinylmethylglycine derivative and an appropriated formyl phthalocyanine or a diformyl phthalocyanine derivative, respectively. ZnP\u2010C<jats:sub>60<\/jats:sub>\u2010ZnPc (<jats:bold>3<\/jats:bold>), (ZnP)<jats:sub>2<\/jats:sub>\u2010ZnPc\u2010(C<jats:sub>60<\/jats:sub>)<jats:sub>2<\/jats:sub> (<jats:bold>6<\/jats:bold>), and (H<jats:sub>2<\/jats:sub>P)<jats:sub>2<\/jats:sub>\u2010ZnPc\u2010(C<jats:sub>60<\/jats:sub>)<jats:sub>2<\/jats:sub> (<jats:bold>5<\/jats:bold>) give rise upon excitation of their ZnP or H<jats:sub>2<\/jats:sub>P components to a sequence of energy and charge\u2010transfer reactions with, however, fundamentally different outcomes. With (ZnP)<jats:sub>2<\/jats:sub>\u2010ZnPc\u2010(C<jats:sub>60<\/jats:sub>)<jats:sub>2<\/jats:sub> (<jats:bold>6<\/jats:bold>) the major pathway is an highly exothermic charge transfer to afford (ZnP)(ZnP<jats:sup>.+<\/jats:sup>)\u2010ZnPc\u2010(C<jats:sub>60<\/jats:sub><jats:sup>.\u2212<\/jats:sup>)(C<jats:sub>60<\/jats:sub>). The lower singlet excited state energy of H<jats:sub>2<\/jats:sub>P (i.e., ca.\u20050.2\u2005eV) and likewise its more anodic oxidation (i.e., ca.\u20050.2\u2005V) renders the direct charge transfer in (H<jats:sub>2<\/jats:sub>P)<jats:sub>2<\/jats:sub>\u2010ZnPc\u2010(C<jats:sub>60<\/jats:sub>)<jats:sub>2<\/jats:sub> (<jats:bold>5<\/jats:bold>) not competitive. Instead, a transduction of singlet excited state energy prevails to form the ZnPc singlet excited state. This triggers then an intramolecular charge transfer reaction to form exclusively (H<jats:sub>2<\/jats:sub>P)<jats:sub>2<\/jats:sub>\u2010ZnPc<jats:sup>.+<\/jats:sup>\u2010(C<jats:sub>60<\/jats:sub><jats:sup>.\u2212<\/jats:sup>)(C<jats:sub>60<\/jats:sub>). A similar sequence is found for ZnP\u2010C<jats:sub>60<\/jats:sub>\u2010ZnPc (<jats:bold>3<\/jats:bold>).<\/jats:p>","DOI":"10.1002\/chem.201102819","type":"journal-article","created":{"date-parts":[[2012,1,4]],"date-time":"2012-01-04T20:23:07Z","timestamp":1325708587000},"page":"1727-1736","source":"Crossref","is-referenced-by-count":51,"title":["Synthesis and Photophysical Properties of Fullerene\u2013Phthalocyanine\u2013Porphyrin Triads and Pentads"],"prefix":"10.1002","volume":"18","author":[{"given":"Roger F.","family":"Enes","sequence":"first","affiliation":[]},{"given":"Juan\u2010Jos\u00e9","family":"Cid","sequence":"additional","affiliation":[]},{"given":"Anita","family":"Hausmann","sequence":"additional","affiliation":[]},{"given":"Olga","family":"Trukhina","sequence":"additional","affiliation":[]},{"given":"Andreas","family":"Gouloumis","sequence":"additional","affiliation":[]},{"given":"Purificaci\u00f3n","family":"V\u00e1zquez","sequence":"additional","affiliation":[]},{"given":"Jos\u00e9 A. S.","family":"Cavaleiro","sequence":"additional","affiliation":[]},{"given":"Augusto C.","family":"Tom\u00e9","sequence":"additional","affiliation":[]},{"given":"Dirk M.","family":"Guldi","sequence":"additional","affiliation":[]},{"given":"Tom\u00e1s","family":"Torres","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2012,1,3]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9001735"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/b905753f"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar900209b"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/b703405a"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac200779060981"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/B604119C"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500321"},{"key":"e_1_2_6_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500321"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.200305172"},{"key":"e_1_2_6_10_2","unstructured":"\u00a0"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900271s"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9002984"},{"key":"e_1_2_6_13_2","doi-asserted-by":"crossref","unstructured":"Special issue onOrganic Photovoltaics(Eds.: J.\u2010L. Bredas J.\u2005R. Durrant) Acc. Chem. Res.2009 42 1689\u20131857;","DOI":"10.1021\/ar900238j"},{"key":"e_1_2_6_14_2","unstructured":"Special issue onRenewable Energy (Eds.: D. Nocera D.\u2005M. Guldi) Chem. Soc. Rev.2009 38 1\u2013293;"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/B614234F"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050149z"},{"key":"e_1_2_6_17_2","unstructured":"\u00a0"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja902471w"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200701700"},{"key":"e_1_2_6_20_2","volume-title":"Fullerenes: Principles and Applications","year":"2007"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp047105z"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/B208516J"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/B205620H"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/b110270m"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00028a010"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.19970090704"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00011a005"},{"key":"e_1_2_6_28_2","unstructured":"\u00a0"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900254z"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol701444d"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/B613086K"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.08.126"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2006.08.107"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo991843f"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo991505e"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1007\/s007060170140"},{"key":"e_1_2_6_37_2","unstructured":"\u00a0"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700936"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.09.088"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/b711194k"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200600885"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1142\/S108842460700045X"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2006.05.062"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp061844t"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601264"},{"key":"e_1_2_6_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601264"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/B610171B"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/B418345B"},{"key":"e_1_2_6_48_2","unstructured":"Reviews:"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/B614883M"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2005.01.002"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/b800617b"},{"key":"e_1_2_6_52_2","unstructured":"\u00a0"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201003364"},{"key":"e_1_2_6_53_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201003364"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ee00368a"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc02213f"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201002118"},{"key":"e_1_2_6_56_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201002118"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9109677"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1142\/9789814307246_0017"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1142\/S1088424610002689"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200801778"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1038\/nphoton.2009.96"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja078045o"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703106"},{"key":"e_1_2_6_63_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703106"},{"key":"e_1_2_6_64_2","unstructured":"Recent examples:"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp908115e"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp062822"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500558"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/b508478d"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja043283u"},{"key":"e_1_2_6_70_2","unstructured":"\u00a0"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol026427n"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00127a036"},{"key":"e_1_2_6_73_2","unstructured":"\u00a0"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1039\/b818772j"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061723b"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0611770"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20001002)6:19<3600::AID-CHEM3600>3.0.CO;2-0"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201102819","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201102819","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:15:14Z","timestamp":1760296514000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201102819"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,1,3]]},"references-count":82,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2012,2,6]]}},"alternative-id":["10.1002\/chem.201102819"],"URL":"https:\/\/doi.org\/10.1002\/chem.201102819","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,1,3]]}}}