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Deprotonation of acid\u2010unit\u2010appended \u03c0\u2010electronic systems, such as\n                    <jats:italic>meso<\/jats:italic>\n                    \u2010hydroxyporphyrins (MHPs), enables the formation of \u03c0\u2010electronic anions, for which the substituents modulate the electronic states and assembly modes. In this study, MHP Pt\n                    <jats:sup>II<\/jats:sup>\n                    complex anions, bearing electron\u2010donating phenyl groups and electron\u2010withdrawing C\n                    <jats:sub>6<\/jats:sub>\n                    F\n                    <jats:sub>5<\/jats:sub>\n                    groups, formed various ion pairs in combination with cations, including triazatriangulenium and porphyrin Au\n                    <jats:sup>III<\/jats:sup>\n                    complex cations. Single\u2010crystal X\u2010ray analysis revealed solid\u2010state ion\u2010pairing assemblies of the MHP Pt\n                    <jats:sup>II<\/jats:sup>\n                    complex anions with charge\u2010by\u2010charge packing modes, where the arrangements of the components were dependent on the peripheral substituents and coexisting countercations. Hirshfeld surface analysis and energy decomposition analysis (EDA) calculations revealed that ion\u2010pairing assembly modes were mainly governed by\n                    <jats:sup>\n                      <jats:italic>i<\/jats:italic>\n                    <\/jats:sup>\n                    \u03c0\u2013\n                    <jats:sup>\n                      <jats:italic>i<\/jats:italic>\n                    <\/jats:sup>\n                    \u03c0 interactions between the MHP Pt\n                    <jats:sup>II<\/jats:sup>\n                    complex anions and countercations.\n                  <\/jats:p>","DOI":"10.1002\/asia.70439","type":"journal-article","created":{"date-parts":[[2025,11,25]],"date-time":"2025-11-25T04:15:08Z","timestamp":1764044108000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Ion\u2010Pairing Assemblies of Deprotonated\n                    <i>Meso<\/i>\n                    \u2010Hydroxyporphyrins as \u03c0\u2010Electronic Anions"],"prefix":"10.1002","volume":"21","author":[{"given":"Miyu","family":"Yokoyama","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry College of Life Sciences Ritsumeikan University  Kusatsu Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroki","family":"Horita","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry College of Life Sciences Ritsumeikan University  Kusatsu Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenqi","family":"Peng","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry College of Life Sciences Ritsumeikan University  Kusatsu Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroki","family":"Tanaka","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry College of Life Sciences Ritsumeikan University  Kusatsu Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9928-1655","authenticated-orcid":false,"given":"Hiromitsu","family":"Maeda","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry College of Life Sciences Ritsumeikan University  Kusatsu Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,11,24]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC00262A"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05915"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010019\u201011080\u20105"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsapm.0c01210"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CS00581J"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202415135"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202404781"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC07576E"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521\u20103773(20001002)39:19<3432::AID\u2010ANIE3432>3.0.CO;2\u2010S"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521\u20103765(20010417)7:8<1773::AID\u2010CHEM17730>3.0.CO;2\u2010F"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2dt12280d"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2019.03.027"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201900422"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/b414683b"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201705814"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201807836"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9DT01514K"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0010\u20108545(00)00258\u20107"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1142\/S1088424602000828"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/B608365J"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b11223"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201504252"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201701354"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201705769"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01066"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC02260A"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09589"},{"key":"e_1_2_8_29_1","unstructured":"M. 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