{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T13:46:01Z","timestamp":1791812761602,"version":"4.3.4"},"reference-count":50,"publisher":"Oxford University Press (OUP)","issue":"19","license":[{"start":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T00:00:00Z","timestamp":1782864000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100014219","name":"National Science Fund for Distinguished Young Scholars","doi-asserted-by":"publisher","award":["22025107"],"award-info":[{"award-number":["22025107"]}],"id":[{"id":"10.13039\/501100014219","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["92461302"],"award-info":[{"award-number":["92461302"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22305190"],"award-info":[{"award-number":["22305190"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004194","name":"Northwest University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004194","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,5]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>Electron transfer is a fundamental process ubiquitous in both natural and artificial systems. The construction of organic redox systems serves as an ideal platform to explore this mechanism. The interconversion between different electronic structures endows them with unique photoelectric properties, enabling their promising applications in fields such as photocatalysis, organic batteries and electrochromic materials. Herein, we present an organic redox system derived from bis(imino)acenaphthene-supported N-heterocyclic carbene, which exhibits two reversible and well-separated redox processes. The different oxidation states could be isolated and fully characterized, including X-ray diffraction. Moreover, the radical cation exhibits strong absorption in the visible-light region and can be easily generated through photoinduction, fulfilling the prerequisites for consecutive photoinduced electron transfer. Therefore, organic redox system can function as a photocatalyst in the reduction of aryl halides. This strategy expands the variety of organic redox systems and provides a novel approach to the development of photocatalysts.<\/jats:p>","DOI":"10.1093\/nsr\/nwag408","type":"journal-article","created":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T14:33:25Z","timestamp":1782916405000},"source":"Crossref","is-referenced-by-count":4,"title":["Annelated N-heterocyclic carbene-derived organic redox system for consecutive visible-light photocatalysis"],"prefix":"10.1093","volume":"13","author":[{"given":"Yu-Jia","family":"Liu","sequence":"first","affiliation":[{"name":"College of Chemistry, Zhengzhou University , Zhengzhou 450001 ,","place":["China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin","family":"Li","sequence":"additional","affiliation":[{"name":"College of Chemistry, Zhengzhou University , Zhengzhou 450001 ,","place":["China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ji-Xin","family":"Man","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Northwest University , Xi\u2019an 710127 ,","place":["China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Can","family":"Chen","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Northwest University , Xi\u2019an 710127 ,","place":["China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Man","family":"Li","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Northwest University , Xi\u2019an 710127 ,","place":["China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jia-Ling","family":"Zhu","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Northwest University , Xi\u2019an 710127 ,","place":["China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ying-Feng","family":"Han","sequence":"additional","affiliation":[{"name":"College of Chemistry, Zhengzhou University , Zhengzhou 450001 ,","place":["China"]},{"name":"College of Chemistry and Materials Science, Northwest University , Xi\u2019an 710127 ,","place":["China"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2026,7,1]]},"reference":[{"key":"2026101209011667700_bib1","doi-asserted-by":"publisher","first-page":"e202410525","DOI":"10.1002\/anie.202410525","article-title":"Directional electron flow in a selenoviologen-based tetracationic cyclophane for enhanced visible-light-driven hydrogen evolution","volume":"63","author":"Li","year":"2024","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib2","doi-asserted-by":"publisher","first-page":"nwaf123","DOI":"10.1093\/nsr\/nwaf123","article-title":"Synergistic ionic modification strategy enhances the stability of naphthalene diimide zwitterions for cost-effective aqueous organic redox flow batteries","volume":"12","author":"Zhang","year":"2025","journal-title":"Natl Sci Rev"},{"key":"2026101209011667700_bib3","doi-asserted-by":"publisher","first-page":"14823","DOI":"10.1021\/jacs.8b08545","article-title":"Pyrylenes: a new class of tunable, redox-switchable, photoexcitable pyrylium\u2013carbene hybrids with three stable redox-states","volume":"140","author":"Antoni","year":"2018","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib4","doi-asserted-by":"publisher","first-page":"3416","DOI":"10.1021\/jacs.3c12766","article-title":"Dicationic acridinium\/carbene hybrids as strongly oxidizing photocatalysts","volume":"146","author":"Sau","year":"2024","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib5","doi-asserted-by":"publisher","first-page":"16718","DOI":"10.1021\/acscatal.5c06069","article-title":"\u03c0-extended heterocycle\/carbene hybrids as geometrically constrained dyes for TADF energy and electron transfer photocatalysis","volume":"15","author":"Ritu","year":"2025","journal-title":"ACS Catal"},{"key":"2026101209011667700_bib6","doi-asserted-by":"publisher","first-page":"10101","DOI":"10.1039\/D4SC02459A","article-title":"Difluorenoheteroles: topological control of \u03c0 conjugation in diradicaloids and mixed-valence radical ions","volume":"15","author":"Prajapati","year":"2024","journal-title":"Chem Sci"},{"key":"2026101209011667700_bib7","doi-asserted-by":"publisher","first-page":"109473","DOI":"10.1016\/j.cclet.2023.109473","article-title":"Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis","volume":"35","author":"Wang","year":"2024","journal-title":"Chin Chem Lett"},{"key":"2026101209011667700_bib8","doi-asserted-by":"publisher","first-page":"725","DOI":"10.1126\/science.1258232","article-title":"Reduction of aryl halides by consecutive visible light-induced electron transfer processes","volume":"346","author":"Ghosh","year":"2014","journal-title":"Science"},{"key":"2026101209011667700_bib9","doi-asserted-by":"publisher","first-page":"832","DOI":"10.1038\/s41929-022-00841-z","article-title":"Visible-light photocatalytic di- and hydro-carboxylation of unactivated alkenes with CO2","volume":"5","author":"Song","year":"2022","journal-title":"Nat Catal"},{"key":"2026101209011667700_bib10","doi-asserted-by":"publisher","first-page":"15521","DOI":"10.1021\/acscatal.4c04032","article-title":"Site-selective pyridine carbamoylation enabled by consecutive photoinduced electron transfer","volume":"14","author":"Wang","year":"2024","journal-title":"ACS Catal"},{"key":"2026101209011667700_bib11","doi-asserted-by":"publisher","first-page":"109138","DOI":"10.1016\/j.cclet.2023.109138","article-title":"Photocatalytic dicarboxylation of strained C\u2013C bonds with CO2 \u00a0via consecutive visible-light-induced electron transfer","volume":"35","author":"Liu","year":"2024","journal-title":"Chin Chem Lett"},{"key":"2026101209011667700_bib12","doi-asserted-by":"publisher","first-page":"76","DOI":"10.1038\/s41586-020-2131-1","article-title":"Discovery and characterization of an acridine radical photoreductant","volume":"580","author":"MacKenzie","year":"2020","journal-title":"Nature"},{"key":"2026101209011667700_bib13","doi-asserted-by":"publisher","first-page":"10047","DOI":"10.1021\/acscatal.2c02991","article-title":"Organophotocatalytic N\u2013O bond cleavage of Weinreb amides: mechanism-guided evolution of a PET to ConPET platform","volume":"12","author":"Soika","year":"2022","journal-title":"ACS Catal"},{"key":"2026101209011667700_bib14","doi-asserted-by":"publisher","first-page":"e202217918","DOI":"10.1002\/anie.202217918","article-title":"Photocatalytic carboxylation of C\u2013N bonds in cyclic amines with CO2 by consecutive visible-light-induced electron transfer","volume":"62","author":"Chen","year":"2023","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib15","doi-asserted-by":"publisher","first-page":"1463","DOI":"10.1002\/cber.19040370245","article-title":"Ueber einen chino\u00efden kohlenwasserstoff","volume":"37","author":"Thiele","year":"1904","journal-title":"Ber Dtsch Chem Ges"},{"key":"2026101209011667700_bib16","doi-asserted-by":"publisher","first-page":"3150","DOI":"10.1002\/cber.19000330369","article-title":"Triphenylmethyl, ein fall von dreiwerthigem kohlenstoff","volume":"33","author":"Gomberg","year":"1900","journal-title":"Ber Dtsch Chem Ges"},{"key":"2026101209011667700_bib17","doi-asserted-by":"publisher","first-page":"7011","DOI":"10.1021\/cr400056a","article-title":"Diradicals","volume":"113","author":"Abe","year":"2013","journal-title":"Chem Rev"},{"key":"2026101209011667700_bib18","doi-asserted-by":"publisher","first-page":"11291","DOI":"10.1021\/acs.chemrev.9b00260","article-title":"Do diradicals behave like radicals?","volume":"119","author":"Stuyver","year":"2019","journal-title":"Chem Rev"},{"key":"2026101209011667700_bib19","doi-asserted-by":"publisher","first-page":"2079","DOI":"10.1021\/ja01064a042","article-title":"One-electron transfer from an olefin to a dicarbonium ion","volume":"86","author":"Hart","year":"1964","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib20","doi-asserted-by":"publisher","first-page":"e202112513","DOI":"10.1002\/anie.202112513","article-title":"Clippane: a mechanically interlocked molecule (MIM) based on molecular tweezers","volume":"61","author":"Ib\u00e1\u00f1ez","year":"2022","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib21","doi-asserted-by":"publisher","first-page":"15412","DOI":"10.1002\/anie.202100914","article-title":"Ion mobility mass spectrometry uncovers guest-induced distortions in a supramolecular organometallic metallosquare","volume":"60","author":"Vicent","year":"2021","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib22","doi-asserted-by":"publisher","first-page":"13415","DOI":"10.1039\/d4sc03661a","article-title":"A corannulene-based metallobox for the encapsulation of fullerenes","volume":"15","author":"Ib\u00e1\u00f1ez","year":"2024","journal-title":"Chem Sci"},{"key":"2026101209011667700_bib23","doi-asserted-by":"publisher","first-page":"10046","DOI":"10.1002\/anie.201702148","article-title":"Cyclic (alkyl) (amino)carbenes (CAACs): recent developments","volume":"56","author":"Melaimi","year":"2017","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib24","doi-asserted-by":"publisher","first-page":"18387","DOI":"10.1039\/D4SC05740F","article-title":"Uncovering diverse reactivity of NHCs with diazoalkane: C\u2013H activation, C=C bond formation, and access to N-heterocyclic methylenehydrazine","volume":"15","author":"Balayan","year":"2024","journal-title":"Chem Sci"},{"key":"2026101209011667700_bib25","doi-asserted-by":"publisher","first-page":"e22286","DOI":"10.1002\/anie.202522286","article-title":"Crystalline 90\u00b0-twisted carbon-centered non-kekul\u00e9 diradical derived from N-heterocyclic carbene","volume":"65","author":"Li","year":"2026","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib26","doi-asserted-by":"publisher","first-page":"2679","DOI":"10.1007\/s11426-024-2003-0","article-title":"NHC-derived carbon-centered luminescent radicals with short-wavelength emission via suppression of Kasha\u2019s rule","volume":"67","author":"Chen","year":"2024","journal-title":"Sci China Chem"},{"key":"2026101209011667700_bib27","doi-asserted-by":"publisher","first-page":"6367","DOI":"10.1021\/jacs.4c18599","article-title":"Isomeric azulene-based carbon-centered radicals derived from N-heterocyclic carbenes","volume":"147","author":"Li","year":"2025","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib28","doi-asserted-by":"publisher","first-page":"4970","DOI":"10.1039\/C8SC01209A","article-title":"Kekul\u00e9 diradicaloids derived from a classical N-heterocyclic carbene","volume":"9","author":"Rottsch\u00e4fer","year":"2018","journal-title":"Chem Sci"},{"key":"2026101209011667700_bib29","doi-asserted-by":"publisher","first-page":"5838","DOI":"10.1002\/anie.201713346","article-title":"N-heterocyclic carbene analogues of Thiele and Chichibabin hydrocarbons","volume":"57","author":"Rottsch\u00e4fer","year":"2018","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib30","doi-asserted-by":"publisher","first-page":"6729","DOI":"10.1002\/anie.201915802","article-title":"CAAC-based Thiele and Schlenk hydrocarbons","volume":"59","author":"Maiti","year":"2020","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib31","doi-asserted-by":"publisher","first-page":"16464","DOI":"10.1021\/acs.joc.1c01827","article-title":"Diamidocarbene-based Thiele and Tschitschibabin hydrocarbons: carbonyl functionalized Kekul\u00e9 diradicaloids","volume":"86","author":"Maiti","year":"2021","journal-title":"J Org Chem"},{"key":"2026101209011667700_bib32","doi-asserted-by":"publisher","first-page":"4915","DOI":"10.1002\/ejic.200600545","article-title":"Silver, palladium and rhodium complexes of acenaphthylene-anullated N-heterocyclic carbene ligands: a comparative study","author":"T\u00fcrkmen","year":"2006","journal-title":"Eur J Inorg Chem"},{"key":"2026101209011667700_bib33","doi-asserted-by":"publisher","first-page":"972","DOI":"10.3390\/catal11080972","article-title":"Acenaphthene-based N-heterocyclic carbene metal complexes: synthesis and application in catalysis","volume":"11","author":"Baczewska","year":"2021","journal-title":"Catalysts"},{"key":"2026101209011667700_bib34","doi-asserted-by":"publisher","first-page":"4478","DOI":"10.1002\/chem.202003923","article-title":"BIAN-NHC ligands in transition-metal-catalysis: a perfect union of sterically encumbered, electronically tunable N-heterocyclic carbenes?","volume":"27","author":"Chen","year":"2021","journal-title":"Chem Eur J"},{"key":"2026101209011667700_bib35","doi-asserted-by":"publisher","first-page":"13643","DOI":"10.1021\/jacs.2c04043","article-title":"Enantio- and regioselective Ni-catalyzed para-C\u2212H alkylation of pyridines with styrenes via intermolecular hydroarylation","volume":"144","author":"Ma","year":"2022","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib36","doi-asserted-by":"publisher","first-page":"662","DOI":"10.1126\/science.ade0760","article-title":"Dynamic kinetic asymmetric arylation and alkenylation of ketones","volume":"379","author":"Ruan","year":"2023","journal-title":"Science"},{"key":"2026101209011667700_bib37","doi-asserted-by":"publisher","first-page":"14428","DOI":"10.1021\/jacs.1c06464","article-title":"Air-\/heat-stable crystalline carbon-centered radicals derived from an annelated N-heterocyclic carbene","volume":"143","author":"Zhao","year":"2021","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib38","doi-asserted-by":"publisher","first-page":"1076","DOI":"10.1039\/D3QO01644G","article-title":"Isolation and characterization of an annelated N-heterocyclic carbene stabilized Breslow enolate","volume":"11","author":"Li","year":"2024","journal-title":"Org Chem Front"},{"key":"2026101209011667700_bib39","doi-asserted-by":"publisher","first-page":"6004","DOI":"10.1021\/ja00279a056","article-title":"The molecular structures of Thiele\u2019s and Chichibabin\u2019s hydrocarbons","volume":"108","author":"Montgomery","year":"1986","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib40","doi-asserted-by":"publisher","first-page":"9004","DOI":"10.1021\/jacs.3c13310","article-title":"Dianionic and neutral diboron-centered classical diradicaloids","volume":"146","author":"Das","year":"2024","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib41","doi-asserted-by":"publisher","first-page":"6706","DOI":"10.1021\/acs.chemrev.8b00233","article-title":"Electrochemical arylation reaction","volume":"118","author":"Waldvogel","year":"2018","journal-title":"Chem Rev"},{"key":"2026101209011667700_bib42","doi-asserted-by":"publisher","first-page":"6520","DOI":"10.1002\/anie.201912753","article-title":"Nickel-catalyzed electrochemical reductive relay cross-coupling of alkyl halides to aryl halides","volume":"59","author":"Jiao","year":"2020","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib43","doi-asserted-by":"publisher","first-page":"23438","DOI":"10.1002\/anie.202010682","article-title":"Ligand control of palladium-catalyzed site-selective \u03b1- and \u03b3-arylation of \u03b1,\u03b2-unsaturated ketones with (hetero)aryl halides","volume":"59","author":"Yuen","year":"2020","journal-title":"Angew Chem Int Ed"},{"key":"2026101209011667700_bib44","doi-asserted-by":"publisher","first-page":"5000","DOI":"10.1021\/acscatal.2c00173","article-title":"Tuning redox states of phenalenyl-based molecules by consecutive reduction toward transition metal-free Heck-type C\u2013C cross-coupling","volume":"12","author":"Banik","year":"2022","journal-title":"ACS Catal"},{"key":"2026101209011667700_bib45","doi-asserted-by":"publisher","first-page":"1268","DOI":"10.1038\/s41929-025-01457-9","article-title":"Illuminating the transformation of photocatalysts in light-driven organic synthesis","volume":"8","author":"Li","year":"2025","journal-title":"Nat Catal"},{"key":"2026101209011667700_bib46","doi-asserted-by":"publisher","first-page":"714","DOI":"10.1055\/s-0035-1561297","article-title":"Experimental and calculated electrochemical potentials of common organic molecules for applications to single-electron redox chemistry","volume":"27","author":"Roth","year":"2016","journal-title":"Synlett"},{"key":"2026101209011667700_bib47","doi-asserted-by":"publisher","first-page":"255","DOI":"10.1021\/ar020230d","article-title":"Bond dissociation energies of organic molecules","volume":"36","author":"Blanksby","year":"2003","journal-title":"Acc Chem Res"},{"key":"2026101209011667700_bib48","doi-asserted-by":"publisher","first-page":"13266","DOI":"10.1021\/jacs.1c05994","article-title":"Unveiling extreme photoreduction potentials of donor\u2013acceptor cyanoarenes to access aryl radicals from aryl chlorides","volume":"143","author":"Xu","year":"2021","journal-title":"J Am Chem Soc"},{"key":"2026101209011667700_bib49","doi-asserted-by":"publisher","first-page":"10075","DOI":"10.1021\/acs.chemrev.6b00057","article-title":"Organic photoredox catalysis","volume":"116","author":"Romero","year":"2016","journal-title":"Chem Rev"},{"key":"2026101209011667700_bib50","doi-asserted-by":"publisher","first-page":"9392","DOI":"10.1021\/acscatal.3c02515","article-title":"Shining fresh light on complex photoredox mechanisms through isolation of intermediate radical anions","volume":"13","author":"Horsewill","year":"2023","journal-title":"ACS Catal"}],"container-title":["National Science Review"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/academic.oup.com\/nsr\/advance-article-pdf\/doi\/10.1093\/nsr\/nwag408\/68670611\/nwag408.pdf","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/nsr\/article-pdf\/13\/19\/nwag408\/68670611\/nwag408.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/nsr\/article-pdf\/13\/19\/nwag408\/68670611\/nwag408.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T13:01:24Z","timestamp":1791810084000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/nsr\/article\/doi\/10.1093\/nsr\/nwag408\/8723318"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,1]]},"references-count":50,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2026,10,5]]}},"URL":"https:\/\/doi.org\/10.1093\/nsr\/nwag408","relation":{},"ISSN":["2095-5138","2053-714X"],"issn-type":[{"value":"2095-5138","type":"print"},{"value":"2053-714X","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2026,10]]},"published":{"date-parts":[[2026,7,1]]},"article-number":"nwag408"}}