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This illustrates the potential use of halogen bonding and isoindoline nitroxide tectons for the assembly of organic spin systems.<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p><jats:p>The isoindoline nitroxide 1,1,3,3\u2010tetramethylisoindolin\u20102\u2010yloxyl (TMIO) and 1,4\u2010diiodotetrafluorobenzene readily form a discrete 2:1 complex that shows evidence of relatively strong N\uf8ffO<jats:sup>.<\/jats:sup>\u22c5\u22c5\u22c5I halogen bonding. This interaction was characterized in the solid state by single\u2010crystal X\u2010ray analysis, thermal analysis, and vibrational spectroscopy (IR and Raman), backed by density functional theory calculations. EPR spectroscopy performed on a solution of TMIO in pentafluoroiodobenzene, a halogen\u2010bonding donor, indicates that halogen bonding induces an increase in electron density at the nitroxide nitrogen nucleus and an increase in the nitroxide rotational correlation time. Our findings demonstrate the potential of utilizing halogen\u2010bonding interactions to promote the self\u2010assembly of new isoindoline nitroxide tectons for the preparation of organic spin systems.<\/jats:p>","DOI":"10.1002\/chem.200801920","type":"journal-article","created":{"date-parts":[[2009,3,12]],"date-time":"2009-03-12T05:54:13Z","timestamp":1236837253000},"page":"4156-4164","source":"Crossref","is-referenced-by-count":96,"title":["Halogen Bonding between an Isoindoline Nitroxide and 1,4\u2010Diiodotetrafluorobenzene: New Tools and Tectons for Self\u2010Assembling Organic Spin Systems"],"prefix":"10.1002","volume":"15","author":[{"given":"Graeme\u2005R.","family":"Hanson","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul","family":"Jensen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"John","family":"McMurtrie","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Llew","family":"Rintoul","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aaron\u2005S.","family":"Micallef","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,4,3]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1080\/1061027031000078248"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20010618)7:12<2511::AID-CHEM25110>3.0.CO;2-T"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/pola.21725"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0400995"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00476-2"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9530002622"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100891a049"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp993415j"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9810686"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1359-0294(03)00055-4"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.12.088"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(72)80136-2"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00769a003"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00429a012"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)00837-0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-1395(200101)14:1<38::AID-POC334>3.0.CO;2-Z"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/0379-6779(94)03054-A"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108768198012786"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.03.033"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp073567b"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp803685r"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800128"},{"key":"e_1_2_6_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800128"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-78759-1_7"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/b002497j"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-458X(199910)37:10<730::AID-MRC530>3.0.CO;2-E"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF03166117"},{"key":"e_1_2_6_27_2","first-page":"48","author":"Giroud A. 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