{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,26]],"date-time":"2026-08-26T18:01:51Z","timestamp":1787767311106,"version":"build-2784847793"},"reference-count":31,"publisher":"Wiley","issue":"17","license":[{"start":{"date-parts":[[2014,3,18]],"date-time":"2014-03-18T00:00:00Z","timestamp":1395100800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2014,4,22]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>7,8\u2010Dehydropurpurin has attracted much attention owing to the dual 18\u03c0\u2010 and 20\u03c0\u2010electron circuits in its macrocyclic conjugation. The two\u2010fold Pd\u2010catalyzed [3+2] annulation of <jats:italic>meso<\/jats:italic>\u2010bromoporphyrin with 1,4\u2010diphenylbutadiyne furnished 7,8\u2010dehydropurpurin dimers. The 8<jats:sup>a<\/jats:sup>,8<jats:sup>a<\/jats:sup>\u2010linked dimer displays a red\u2010shifted and enhanced absorption band in the NIR region and a small electrochemical HOMO\u2013LUMO band gap as a consequence of efficient conjugation between the two coplanar 7,8\u2010dehydropurpurin units. Treatment of this dimer with <jats:italic>N<\/jats:italic>\u2010bromosuccinimide in chloroform and ethanol gave \u03b2\u2010to\u2010\u03b2 vinylene\u2010bridged porphyrin dimers. Owing to the highly constrained conformations, these dimers exhibit perturbed absorption spectra, small Stokes shifts, and high fluorescence quantum yields.<\/jats:p>","DOI":"10.1002\/anie.201400632","type":"journal-article","created":{"date-parts":[[2014,3,18]],"date-time":"2014-03-18T23:41:33Z","timestamp":1395186093000},"page":"4395-4398","source":"Crossref","is-referenced-by-count":23,"title":["Synthesis of 7,8\u2010Dehydropurpurin Dimers and Their Conversion into Conformationally Constrained \u03b2\u2010to\u2010\u03b2 Vinylene\u2010Bridged Porphyrin Dimers"],"prefix":"10.1002","volume":"53","author":[{"given":"Norihito","family":"Fukui","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hideki","family":"Yorimitsu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jong Min","family":"Lim","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dongho","family":"Kim","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Atsuhiro","family":"Osuka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,3,18]]},"reference":[{"key":"e_1_2_2_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3082999"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200603580"},{"key":"e_1_2_2_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603580"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/b106050n"},{"key":"e_1_2_2_4_2","unstructured":"For benzo\u2010fused 7 8\u2010dehydropurpurins see:"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/b403466j"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b509972b"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0609677"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2008.846"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja8055886"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo2006895"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2020658"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc42831a"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304794"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304794"},{"key":"e_1_2_2_14_2","unstructured":"Although we used NCy2Me (Cy=cyclohexyl) as the base in the previously reported procedures use of NEt3enhanced the yield of2\u2009Niand3\u2009Ni."},{"key":"e_1_2_2_15_2","unstructured":"\u00a0"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00017a059"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0683966"},{"key":"e_1_2_2_18_2","unstructured":"Gaussian\u200909 revision\u2009A.02 M.\u2005J. Frisch. et\u2005al. Gaussian Inc.: Wallingford CT 2009."},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19961081630"},{"key":"e_1_2_2_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199618401"},{"key":"e_1_2_2_20_2","unstructured":"For \u03b2\u2010to\u2010\u03b2 vinylene\u2010bridged porphyrin dimers see:"},{"key":"e_1_2_2_21_2","first-page":"326","volume":"303","author":"Zhilina Z. I.","year":"1988","journal-title":"Dokl. Akad. Nauk SSSR"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)61377-1"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1070\/MC1995v005n02ABEH000450"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-1938"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc12020d"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.201180490"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja971678q"},{"key":"e_1_2_2_28_2","unstructured":"The quantum yield of ZnIItriphenylporphyrin was measured to be 0.023 by our apparatus."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201400632","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201400632","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T19:49:37Z","timestamp":1697485777000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201400632"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,3,18]]},"references-count":31,"journal-issue":{"issue":"17","published-print":{"date-parts":[[2014,4,22]]}},"alternative-id":["10.1002\/anie.201400632"],"URL":"https:\/\/doi.org\/10.1002\/anie.201400632","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,3,18]]}}}