{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:24:17Z","timestamp":1790641457302,"version":"4.1.0"},"reference-count":32,"publisher":"Wiley","issue":"29","license":[{"start":{"date-parts":[[2025,4,21]],"date-time":"2025-04-21T00:00:00Z","timestamp":1745193600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008668","name":"Shorai Foundation for Science and Technology","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008668","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010981","name":"Izumi Science and Technology Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100010981","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,5,22]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    In this study, we prepared stable radical cation salts of racemic and enantiopure double hetero[5]helicene (\n                    <jats:bold>1<\/jats:bold>\n                    ), consisting of two benzo[\n                    <jats:italic>b<\/jats:italic>\n                    ]phenoxazine (\n                    <jats:bold>BPO<\/jats:bold>\n                    ) molecules, using two different counter anions (SbCl\n                    <jats:sub>6<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    and NTf\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    ). The effects of chirality and counter anions on the packing structure and solid\u2010state electronic properties were investigated. X\u2010ray single\u2010crystal analysis revealed that the SbCl\n                    <jats:sub>6<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    anion was positioned above the midpoint of\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                    <\/jats:bold>\n                    in both the racemic and enantiopure crystals of\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                      \u00b7\n                    <\/jats:bold>\n                    SbCl\n                    <jats:sub>6<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    . This alignment resulted from the matching between the curvature of\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                    <\/jats:bold>\n                    and the spherical shape of the SbCl\n                    <jats:sub>6<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    anion, preventing the formation of continuous \u03c0\u2013\u03c0 interactions among\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                    <\/jats:bold>\n                    . In contrast, 1D \u03c0\u2013stacked columns of\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                    <\/jats:bold>\n                    were present in both the racemic and enantiopure\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                      \u00b7\n                    <\/jats:bold>\n                    NTf\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    crystals, as the NTf\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    anions encased the \u03c0\u2010stacked columns of\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                    <\/jats:bold>\n                    . All radical cation salts exhibited distinct melting points, and the enantiopure salts of\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                      \u00b7\n                    <\/jats:bold>\n                    NTf\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    had notably low melting points of 393\u2013395 K, which was 142 K lower than that of\n                    <jats:italic>rac<\/jats:italic>\n                    \u2010\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                      \u00b7\n                    <\/jats:bold>\n                    NTf\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    . ESR and SQUID measurements of the enantiopure\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                      \u00b7\n                    <\/jats:bold>\n                    NTf\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    crystals revealed significant changes in their magnetic properties upon crystal melting. In contrast,\n                    <jats:italic>rac<\/jats:italic>\n                    \u2010\n                    <jats:bold>\n                      1\n                      <jats:sup>\u00b7+<\/jats:sup>\n                      \u00b7\n                    <\/jats:bold>\n                    NTf\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    displayed an unexpected crystal\u2013crystal phase transition near room temperature, accompanied by a thermal hysteresis loop in its magnetic susceptibility.\n                  <\/jats:p>","DOI":"10.1002\/chem.202500942","type":"journal-article","created":{"date-parts":[[2025,4,9]],"date-time":"2025-04-09T22:26:16Z","timestamp":1744237576000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Effects of Chirality and Counter Anions on the Structures and Solid\u2010State Properties of Radical Cation Salts of Benzo[\n                    <i>b<\/i>\n                    ]Phenoxazine\u2010Based Double Heterohelicene"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6503-1607","authenticated-orcid":false,"given":"Daisuke","family":"Sakamaki","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Science Osaka Metropolitan University  Sumiyoshi\u2010ku Osaka 558\u20138585 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiyori","family":"Sekiguchi","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Osaka Metropolitan University  Sumiyoshi\u2010ku Osaka 558\u20138585 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shuichi","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Engineering Science Osaka University  Toyonaka Osaka 560\u20138531 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hideki","family":"Fujiwara","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Osaka Metropolitan University  Sumiyoshi\u2010ku Osaka 558\u20138585 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