{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,23]],"date-time":"2026-03-23T08:09:56Z","timestamp":1774253396241,"version":"3.50.1"},"reference-count":141,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2026,2,26]],"date-time":"2026-02-26T00:00:00Z","timestamp":1772064000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,2,26]],"date-time":"2026-02-26T00:00:00Z","timestamp":1772064000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemistryOpen"],"published-print":{"date-parts":[[2026,3]]},"abstract":"\n Impact of fluorination on crystal and molecular structure, heteroatom reactivity, and solid\u2010state magnetic properties of thermally\u2010stable\n \u03c0<\/jats:italic>\n \u2010radicals is studied experimentally and computationally with 1,3,2\u2010benzodithiazolyl\n 1<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n and its 4,7\u2010difluoro, 4,5,6,7\u2010tetrafluoro, and 4,7\u2010difluoro\u20105,6\u2010(hexafluoropropane\u20101,3\u2010diyl) derivatives\n 2<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n \u2010\n 4<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n , respectively. Radicals\n 2<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n \u2010\n 4<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n are isolated by vacuum thermolysis of their unusual covalent 2:1 adducts with 7,7,8,8\u2010tetracyanoquinodimethane. The impact of fluorination on reactivity is evidenced by transformation of\n 2<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n \u2010\n 4<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n and\n 2<\/jats:bold>\n \n +<\/jats:bold>\n <\/jats:sup>\n \u2010\n 4<\/jats:bold>\n \n +<\/jats:bold>\n <\/jats:sup>\n into corresponding 2H\u20101\u2010oxo\u20101,3,2\u2010benzodithiazoles under the influence of air's or solvents\u2019 moisture; back transformation into the cations under the action of protic acids; and formation of a paramagnetic molecular complex between\n 3<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n and naphthalene, whereas\n 1<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n and octafluoronaphthalene do not exhibit complexation. The crystal structures of\n 3<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n and\n 4<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n reveal a novel packing motif featuring radical pairs linked by four\u2010center interactions that stack into offset\n \u03c0<\/jats:italic>\n \u2010columns, forming a unique zip\u2010\n \u03c0<\/jats:italic>\n \u2010stack synthon that incorporates head\u2010over\u2010tail\n \u03c0<\/jats:italic>\n \u2010pairs of radicals. Despite the formation of\n \u03c0<\/jats:italic>\n \u2010pairs, polycrystalline\n 3<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n and\n 4<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n display a nonzero effective magnetic moment that rises with temperature above 200 K, although the values remain significantly lower than those of the high\u2010temperature polymorphs of magnetically\u2010bistable\n 1<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n and\n 2<\/jats:bold>\n \n \u00b7<\/jats:bold>\n <\/jats:sup>\n . This behavior can be rationalized by different magnetic topologies and values of spin exchange between the radicals.\n <\/jats:p>","DOI":"10.1002\/open.202500561","type":"journal-article","created":{"date-parts":[[2026,3,8]],"date-time":"2026-03-08T23:41:59Z","timestamp":1773013319000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Stable 1,3,2\u2010Benzodithiazolyl Radicals: Modification of Reactivity, Crystal Packing, and Solid State Magnetic Properties by Fluorination"],"prefix":"10.1002","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0009-0002-4104-2357","authenticated-orcid":false,"given":"Alexander A.","family":"Buravlev","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry Siberian Branch of the Russian Academy of Sciences Novosibirsk Russia"},{"name":"Department of Natural Sciences National Research University \u2013 Novosibirsk State University Novosibirsk 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