{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T02:58:43Z","timestamp":1790305123156,"version":"4.1.0"},"reference-count":71,"publisher":"Wiley","issue":"49","license":[{"start":{"date-parts":[[2014,10,8]],"date-time":"2014-10-08T00:00:00Z","timestamp":1412726400000},"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":[[2014,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>O<jats:sub>6<\/jats:sub>\u2010Corona[3]arene[3]tetraazines, a new class of macrocyclic compounds, were synthesized efficiently in a one\u2010pot reaction from the nucleophilic aromatic substitution reaction between 1,4\u2010dihydroxybenzene derivatives and 3,6\u2010dichlorotetrazine in warm acetonitrile. In the crystalline structure, the resulting macrocycles adopt highly symmetric structures of a regular hexagonal cavity with all bridging oxygen atoms and tetrazine rings located on the same plane with phenylene units orthogonally orientated. The constitutional aromatic rings are able to rotate around the macrocyclic annulus, depending on the steric effect of the substituents and temperature, in solution. The electron\u2010deficient nature revealed by cyclic voltammetry, differential pulse voltammetry, and characteristic absorbances at a visible region show the O<jats:sub>6<\/jats:sub>\u2010corona[3]arene[3]tetrazines to be suitable macrocyclic receptors for electron\u2010rich guests.<\/jats:p>","DOI":"10.1002\/anie.201407670","type":"journal-article","created":{"date-parts":[[2014,10,8]],"date-time":"2014-10-08T20:37:40Z","timestamp":1412800660000},"page":"13548-13552","source":"Crossref","is-referenced-by-count":105,"title":["Synthesis, Structure, and Properties of O<sub>6<\/sub>\u2010Corona[3]arene[3]tetrazines"],"prefix":"10.1002","volume":"53","author":[{"given":"Qing\u2010Hui","family":"Guo","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhan\u2010Da","family":"Fu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liang","family":"Zhao","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mei\u2010Xiang","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,10,8]]},"reference":[{"key":"e_1_2_2_1_2","volume-title":"Comprehensive Supramolecular Chemistry","year":"1996"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198810211"},{"key":"e_1_2_2_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881000805"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198800891"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881000110"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198810093"},{"key":"e_1_2_2_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881000804"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1142\/p124"},{"key":"e_1_2_2_6_2","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/9781847550293"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(01)00346-0"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462839"},{"key":"e_1_2_2_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462839"},{"key":"e_1_2_2_10_2","volume-title":"Core Concepts in Supramolecular Chemistry and Nanochemistry","author":"Steed J. W.","year":"2007"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar500212y"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar040152p"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200805340"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200805340"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1031"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja412615h"},{"key":"e_1_2_2_16_2","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200351975"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200351975"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0465092"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/b809287g"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar200108c"},{"key":"e_1_2_2_21_2","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/b718356a"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1007\/7081_2007_094"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050565j"},{"key":"e_1_2_2_25_2","unstructured":"\u00a0"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja807126u"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902617"},{"key":"e_1_2_2_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200902617"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905659"},{"key":"e_1_2_2_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200905659"},{"key":"e_1_2_2_29_2","first-page":"483","author":"Sisto T. J.","year":"2012","journal-title":"Synlett"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar300055x"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201300035"},{"key":"e_1_2_2_32_2","unstructured":"\u00a0"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja711260m"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200904765"},{"key":"e_1_2_2_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200904765"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10847-011-0027-2"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar2003418"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC00738G"},{"key":"e_1_2_2_38_2","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801705"},{"key":"e_1_2_2_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801705"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja310834w"},{"key":"e_1_2_2_41_2","unstructured":"Based on IUPAC nomenclature the designed and synthesized macrocycles are named as 2 4 6 8 10 12\u2010hexoxa\u20101 5 9(3 6)\u2010tritetrazina\u20103 7 11(1 4)\u2010tribenzacyclododecaphanes. According to the shape of macrocycles we suggest a simple and general term corona[n]arenes to name macrocycles which are composed ofpara\u2010(het)arylenes and heteroatoms in an alternative manner. While the type and the number of linking heteroatoms are prefixed to corona the bracketed number(s) followed by the name of (het)aromatic rings after corona indicate the aromatic components. O6\u2010Corona[3]arene[3]tetrazine for example means a macrocycle consisting alternately of three phenylene units and three tetrazinylene units that are bridged by six oxygen atoms."},{"key":"e_1_2_2_42_2","unstructured":"\u00a0"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.2533\/chimia.2011.939"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar300080f"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)91042-1"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0609982"},{"key":"e_1_2_2_47_2","unstructured":"\u00a0"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570280844"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570350616"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1080\/07370659908201796"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/b613223e"},{"key":"e_1_2_2_52_2","unstructured":"\u00a0"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100699a054"},{"key":"e_1_2_2_54_2","volume-title":"Applications of Dynamic NMR Spectroscopy to Organic Chemistry","author":"\u014cki M.","year":"1985"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00032a005"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900357e"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.457153"},{"key":"e_1_2_2_58_2","unstructured":"\u00a0"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0jm03365k"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.19950070608"},{"key":"e_1_2_2_61_2","unstructured":"CCDC\u20051015930 (3\u2009a) 1015931 (3\u2009b) 1015932 (3\u2009d) 1015933 (3\u2009g) and 1015934 ([Et4N]3[3\u2009gCl3]) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201407670","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201407670","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,17]],"date-time":"2023-10-17T06:48:51Z","timestamp":1697525331000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201407670"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,10,8]]},"references-count":71,"journal-issue":{"issue":"49","published-print":{"date-parts":[[2014,12]]}},"alternative-id":["10.1002\/anie.201407670"],"URL":"https:\/\/doi.org\/10.1002\/anie.201407670","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,10,8]]}}}