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Here we establish nitrogen speciation as a molecular descriptor for governing oxygen activation in metal\u2010free macrocycles. Guided by density functional theory, we designed a tetra\u2010aza macrocycle with nearly exclusive pyridinic nitrogen, distinct from the mixed\u2010nitrogen environments of conventional porphyrins and phthalocyanines. This configuration uniquely stabilizes the key *OOH intermediate while strengthening interfacial electronic coupling with carbon supports. When integrated into a flow\u2010cell electrolyzer, the catalyst achieves \u223c95% H\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    Faradaic efficiency and stability for over 800 h at 300\u00a0mA cm\n                    <jats:sup>\u22122<\/jats:sup>\n                    , continuously generating &gt;3\u00a0wt.% H\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    . Furthermore, in situ generated reactive oxygen species enable selective ambient upgrading of furfural to oxime (&gt;90% yield). Techno\u2010economic analysis supports the economic viability of the process. By linking well\u2010defined nitrogen coordination to scalable device performance, this work provides a blueprint for translating molecular precision into practical electrocatalytic manufacturing.\n                  <\/jats:p>","DOI":"10.1002\/anie.1507031","type":"journal-article","created":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T11:46:13Z","timestamp":1786016773000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Nitrogen Speciation Dictates Industrial\u2010Current Oxygen Reduction in Metal\u2010Free Macrocycles for H\n                    <sub>2<\/sub>\n                    O\n                    <sub>2<\/sub>\n                    Synthesis"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5273-4709","authenticated-orcid":false,"given":"Zhen","family":"Liu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Chemo and Biosensing, National Graduate College for Elite Engineers and College of Chemistry and Chemical Engineering Hunan University Changsha China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yang","family":"Hu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo and Biosensing, National Graduate College for Elite Engineers and College of Chemistry and Chemical Engineering Hunan University Changsha China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-6555-5828","authenticated-orcid":false,"given":"Bufeng","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemo and Biosensing, National Graduate College for Elite Engineers and College of Chemistry and Chemical Engineering Hunan University Changsha China"},{"name":"Hunan Provincial Polyimide Film Engineering Technology Research Center Zhuzhou Shidai Huaxin New Material Technology Co., Ltd.  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Zhuzhou China"},{"name":"Department of Chemical Engineering The University of Melbourne  Parkville Victoria Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,8,6]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929\u2010025\u201001454\u2010y"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44160\u2010025\u201000756\u20100"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.add7417"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44286\u2010025\u201000210\u20100"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aay1844"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010025\u201001894\u2010w"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44286\u2010024\u201000076\u20108"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aad0832"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010025\u201066161\u20105"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929\u2010023\u201000924\u20105"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929\u2010024\u201001190\u20109"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586\u2010019\u20101760\u20108"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41563\u2010024\u201001998\u20107"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586\u2010024\u201007958\u20100"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44286\u2010023\u201000009\u2010x"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.abl4822"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929\u2010023\u201001012\u20104"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c10633"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41560\u2010022\u201001062\u20101"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202502430"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mtphys.2023.101158"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202513010"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2025.112148"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpclett.2c02684"},{"key":"e_1_2_8_26_1","first-page":"1","article-title":"Structure\u2010Activity Relationships of 2\u2010Pyridinone Derivatives for HIV\u20101\u2010Specific Reverse Transcriptase Inhibitors: With ETM and ANNs","volume":"1","author":"Saymer H. 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