{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T16:05:59Z","timestamp":1789574759858,"version":"build-2803163510"},"reference-count":60,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T00:00:00Z","timestamp":1789516800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T00:00:00Z","timestamp":1789516800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy","doi-asserted-by":"publisher","award":["DE\u2010AC02\u201006CH11357"],"award-info":[{"award-number":["DE\u2010AC02\u201006CH11357"]}],"id":[{"id":"10.13039\/100000015","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy","doi-asserted-by":"publisher","award":["DE\u2010SC0024064"],"award-info":[{"award-number":["DE\u2010SC0024064"]}],"id":[{"id":"10.13039\/100000015","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Organic electrode materials (OEMs) offer a sustainable alternative to inorganic cathodes but typically suffer from low intrinsic electronic conductivity. The material historically reported as bis\u2010tetraaminobenzoquinone (TAQ) exhibits bulk conductivity two orders of magnitude higher than its close analogue tetraaminophenazine\u2010tetraone (TAPT), despite their common precursor and nearly identical short\u2010range structure. This disparity has previously been attributed to distinct molecular skeletons, with TAQ proposed to adopt a piperazine\u2010type linkage and TAPT a pyrazine ring. Here, combining synchrotron x\u2010ray scattering, solid\u2010state\n                    <jats:sup>15<\/jats:sup>\n                    N and\n                    <jats:sup>13<\/jats:sup>\n                    C nuclear magnetic resonance (NMR), microcrystal electron diffraction (MicroED), continuous\u2010wave and pulsed electron paramagnetic resonance (EPR) spectroscopy, we show that \u201cTAQ\u201d has the same pyrazine\u2010based molecular structure as TAPT, with no evidence for piperazine core or keto\u2013enol tautomerization. Their key difference lies in synthesis\u2010dependent degree of crystallinity: \u201cTAQ\u201d exhibits greater long\u2010range structural coherence and a crystallographically resolved intermolecular hydrogen\u2010bonding network, whereas TAPT is more disordered. EPR further shows that the higher structural order in \u201cTAQ\u201d is associated with a strongly delocalized \u03c0\u2010spin manifold, while TAPT favors localized or weakly delocalized radicals and stronger local spin coupling. These findings identify degree of crystallinity and hydrogen\u2010bonding order as key structural features associated with radical delocalization and enhanced conductivity in organic electrodes.\n                  <\/jats:p>","DOI":"10.1002\/anie.2483808","type":"journal-article","created":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T15:12:33Z","timestamp":1789571553000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Hydrogen\u2010Bonding Order Associated With Radical Delocalization in Layered Organic Cathode Materials"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1208-5761","authenticated-orcid":false,"given":"Alae Eddine","family":"Lakraychi","sequence":"first","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Department of Electrical and Computer Engineering University of Houston  Houston Texas USA"},{"name":"Texas Center for Superconductivity University of Houston  Houston Texas USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-1420-9788","authenticated-orcid":false,"given":"Zeqian","family":"Zhang","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Department of Chemistry University of Washington  Seattle Washington USA"},{"name":"Physical and Computational Sciences Directorate Pacific Northwest National Laboratory  Richland Washington USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8484-243X","authenticated-orcid":false,"given":"Oliver","family":"Lin","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Illinois  Urbana Illinois USA"},{"name":"Materials Research Laboratory University of Illinois  Urbana Illinois USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eric D","family":"Walter","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Physical and Computational Sciences Directorate Pacific Northwest National Laboratory  Richland Washington USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1176-704X","authenticated-orcid":false,"given":"Jiaqi","family":"Wang","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"X\u2010ray Science Division Argonne National Laboratory  Lemont Illinois USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0834-1507","authenticated-orcid":false,"given":"Harshan Reddy","family":"Gopidi","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Department of Electrical and Computer Engineering University of Houston  Houston Texas USA"},{"name":"Texas Center for Superconductivity University of Houston  Houston Texas USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3912-1195","authenticated-orcid":false,"given":"Eliot F.","family":"Woods","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Energy and Environment Directorate Pacific Northwest National Laboratory  Richland Washington USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1427-3571","authenticated-orcid":false,"given":"Ruozhu","family":"Feng","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Energy and Environment Directorate Pacific Northwest National Laboratory  Richland Washington USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5453-4695","authenticated-orcid":false,"given":"Wei","family":"Wang","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Energy and Environment Directorate Pacific Northwest National Laboratory  Richland Washington USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5168-9253","authenticated-orcid":false,"given":"Pieremanuele","family":"Canepa","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Department of Electrical and Computer Engineering University of Houston  Houston Texas USA"},{"name":"Texas Center for Superconductivity University of Houston  Houston Texas USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3925-4174","authenticated-orcid":false,"given":"Brett A.","family":"Helms","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"The Molecular Foundry Lawrence Berkeley National Laboratory  Berkeley California USA"},{"name":"Materials Sciences Division Lawrence Berkeley National Laboratory  Berkeley California USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0051-3661","authenticated-orcid":false,"given":"Kamila M.","family":"Wiaderek","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"X\u2010ray Science Division Argonne National Laboratory  Lemont Illinois USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1968-441X","authenticated-orcid":false,"given":"Qian","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Illinois  Urbana Illinois USA"},{"name":"Materials Research Laboratory University of Illinois  Urbana Illinois USA"},{"name":"Department of Materials Science and Engineering University of Illinois  Urbana Illinois USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8785-5030","authenticated-orcid":false,"given":"Yan","family":"Yao","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Department of Electrical and Computer Engineering University of Houston  Houston Texas USA"},{"name":"Texas Center for Superconductivity University of Houston  Houston Texas USA"},{"name":"Department of Earth and Environmental Engineering Columbia University  New York New York USA"},{"name":"Columbia Climate School Columbia University  New York New York USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7417-0991","authenticated-orcid":false,"given":"Ying","family":"Chen","sequence":"additional","affiliation":[{"name":"Energy Storage Research Alliance Argonne National Laboratory  Lemont Illinois USA"},{"name":"Physical and Computational Sciences Directorate Pacific Northwest National Laboratory  Richland Washington USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,16]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00482"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570\u2010020\u20100160\u20109"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsenergylett.1c01368"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41578\u2010022\u201000478\u20101"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44359\u2010025\u201000079\u20105"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41563\u2010019\u20100435\u2010z"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3TC03058J"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/256394a0"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00314"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr941181o"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201607820"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aao7287"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586\u2010026\u201010174\u20107"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200602584"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/app.28470"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpowsour.2007.10.086"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b02290"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c06527"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC05679C"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmat4766"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c04591"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c02378"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2025.102590"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2EE00566B"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202421008"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c18105"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ensm.2019.05.001"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.0c03642"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.1c00793"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202317393"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/aenm.202404116"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms2352"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmat4768"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2020.10.001"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712895"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.joule.2023.03.011"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2EE02961H"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.3c01478"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/smll.202401481"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c17713"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1007\/s44503\u2010026\u201000005\u20101"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.6c00267"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202207221"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0009\u20102509(00)00459\u20100"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja972368a"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.7.140"},{"key":"e_1_2_8_48_1","volume-title":"Electron Paramagnetic Resonance: Elementary Theory and Practical Applications","author":"Weil J. A.","year":"2007"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030639w"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRev.98.349"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.5802\/crphys.164"},{"key":"e_1_2_8_52_1","first-page":"10","volume-title":"Electron Spin Resonance Spectroscopy of Organic Radicals","year":"2003"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC01932E"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2024.07.011"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3tb20193g"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010026\u201070370\u2010x"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.0c18928"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010019\u201012248\u20109"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.orgel.2014.09.038"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/d0sc03521a"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja072607m"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.2483808","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.2483808","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.2483808","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T15:12:34Z","timestamp":1789571554000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.2483808"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,16]]},"references-count":60,"alternative-id":["10.1002\/anie.2483808"],"URL":"https:\/\/doi.org\/10.1002\/anie.2483808","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,16]]},"assertion":[{"value":"2026-06-02","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-07","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-16","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e2483808"}}