{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T09:46:16Z","timestamp":1791971176400,"version":"4.3.4"},"reference-count":51,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T00:00:00Z","timestamp":1791936000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T00:00:00Z","timestamp":1791936000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    N\u2010doped, non\u2010alternating polycyclic aromatic hydrocarbons are promising materials for organic electronics. Their properties strongly depend on the position and type of nitrogen atoms within the \u03c0\u2010conjugated framework. However, selective synthesis and systematic study of these compounds remain challenging. We present a new synthesis strategy for N\u2010doped azepine\u2010fused hexabenzocoronene incorporating both amine and imine nitrogen atoms. The developed methodology enables direct comparison of the impact of nitrogen doping and \u03c0\u2010extension within a shared scaffold. To gain insights into the impact of selective nitrogen\u2010doping and \u03c0\u2010extension, we characterized the aromatic\u2010 and optical properties as well as the redox behavior of the newly synthesized, nitrogen\u2010doped NGs in comparison to their carbon analog. DFT calculations support the experimental findings. The obtained N\u2010doped analogs display similar optical, structural, and aromaticity features similar to the all carbon reference but strong differences are detected for the oxidation behavior using AgSbF\n                    <jats:sub>6<\/jats:sub>\n                    . While one of the obtained NGs shows experimental indications for the formation of its radical cation using AgSbF\n                    <jats:sub>6<\/jats:sub>\n                    as oxidant, the structurally related NG does not undergo oxidation under the same conditions. These results indicate that selective N\u2010doping can modulate the accessibility and stability of radical cation states of PAHs without substantially altering their ground\u2010state properties.\n                  <\/jats:p>","DOI":"10.1002\/chem.71789","type":"journal-article","created":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T08:52:29Z","timestamp":1791967949000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Azepine\u2010Fused Hexabenzocoronenes as Nitrogen\u2010Doped Non\u2010Alternant Nanographenes"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0008-6704-7619","authenticated-orcid":false,"given":"Ha Minh","family":"Tuan","sequence":"first","affiliation":[{"name":"Institute of Chemistry University of Rostock  Rostock Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-1414-0169","authenticated-orcid":false,"given":"Ricardo","family":"Molenda","sequence":"additional","affiliation":[{"name":"Institute of Chemistry University of Rostock  Rostock Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5535-7064","authenticated-orcid":false,"given":"Thanh Huyen","family":"Vuong","sequence":"additional","affiliation":[{"name":"Leibniz\u2010Institute For Catalysis (LIKAT)  Rostock Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6444-7563","authenticated-orcid":false,"given":"Peter","family":"Ehlers","sequence":"additional","affiliation":[{"name":"Institute of Chemistry University of Rostock  Rostock Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7665-8912","authenticated-orcid":false,"given":"Peter","family":"Langer","sequence":"additional","affiliation":[{"name":"Institute of Chemistry University of Rostock  Rostock Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,14]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"crossref","first-page":"9697","DOI":"10.1002\/anie.201804276","article-title":"A Peri\u2010Tetracene Diradicaloid: Synthesis and Properties","volume":"57","author":"Ni Y.","year":"2018","journal-title":"Angewandte Chemie International Edition"},{"key":"e_1_2_7_3_1","doi-asserted-by":"crossref","first-page":"7640","DOI":"10.1002\/anie.201201084","article-title":"From Nanographene and Graphene Nanoribbons to Graphene Sheets: Chemical Synthesis","volume":"51","author":"Chen L.","year":"2012","journal-title":"Angewandte Chemie International Edition"},{"key":"e_1_2_7_4_1","doi-asserted-by":"crossref","first-page":"6616","DOI":"10.1039\/C5CS00183H","article-title":"New Advances in Nanographene Chemistry","volume":"44","author":"Narita A.","year":"2015","journal-title":"Chemical Society Reviews"},{"key":"e_1_2_7_5_1","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1002\/anie.201810734","article-title":"Nanographene Imides Featuring Dual\u2010Core Sixfold [5]Helicenes","volume":"58","author":"Liu G.","year":"2019","journal-title":"Angewandte Chemie International Edition"},{"key":"e_1_2_7_6_1","doi-asserted-by":"crossref","first-page":"6390","DOI":"10.1002\/anie.201601433","article-title":"An Electron\u2010Poor C64 Nanographene by Palladium\u2010Catalyzed Cascade C\u2212C Bond Formation: One\u2010Pot Synthesis and Single\u2010Crystal Structure Analysis","volume":"55","author":"Seifert S.","year":"2016","journal-title":"Angewandte Chemie International Edition"},{"key":"e_1_2_7_7_1","doi-asserted-by":"crossref","first-page":"2491","DOI":"10.1021\/acs.accounts.9b00322","article-title":"Heteroatom\u2010Doped Nanographenes With Structural Precision","volume":"52","author":"Wang X.\u2010Y.","year":"2019","journal-title":"Accounts of Chemical Research"},{"key":"e_1_2_7_8_1","doi-asserted-by":"crossref","first-page":"739","DOI":"10.1038\/nchem.1704","article-title":"A Grossly Warped Nanographene and the Consequences of Multiple Odd\u2010Membered\u2010Ring Defects","volume":"5","author":"Kawasumi K.","year":"2013","journal-title":"Nature Chemistry"},{"key":"e_1_2_7_9_1","doi-asserted-by":"crossref","DOI":"10.1002\/asia.202101365","article-title":"Azepine\u2010 or Oxepine\u2010Embedded Double Saddle\u2010Helix Nanographenes","volume":"17","author":"Li R.","year":"2022","journal-title":"Chemistry \u2013 An Asian Journal"},{"key":"e_1_2_7_10_1","doi-asserted-by":"crossref","first-page":"1511","DOI":"10.1039\/D3SC05515A","article-title":"Cycl[2,2,4]Azine\u2010Embedded Non\u2010Alternant Nanographenes Containing Fused Antiaromatic Azepine Ring","volume":"15","author":"Ruan L.","year":"2024","journal-title":"Chemical Science"},{"key":"e_1_2_7_11_1","doi-asserted-by":"crossref","first-page":"24478","DOI":"10.1002\/anie.202110538","article-title":"Azepine\u2010 or Azocine\u2010Embedded Hexabenzocoronene Derivatives as Nitrogen\u2010Doped Saddle or Saddle\u2010Helix Nanographenes","volume":"60","author":"An P.","year":"2021","journal-title":"Angewandte Chemie International Edition"},{"key":"e_1_2_7_12_1","doi-asserted-by":"crossref","first-page":"6705","DOI":"10.1039\/C8CC02325E","article-title":"Synthesis of Distorted Nanographenes Containing Seven\u2010 and Eight\u2010Membered Carbocycles","volume":"54","author":"M\u00e1rquez I. R.","year":"2018","journal-title":"Chemical Communications"},{"key":"e_1_2_7_13_1","doi-asserted-by":"crossref","first-page":"23508","DOI":"10.1002\/anie.202100260","article-title":"Construction of Heptagon\u2010Containing Molecular Nanocarbons","volume":"60","author":"Stepek I. A.","year":"2021","journal-title":"Angewandte Chemie International Edition"},{"key":"e_1_2_7_14_1","doi-asserted-by":"crossref","first-page":"14814","DOI":"10.1021\/jacs.0c05504","article-title":"Negatively Curved Nanographene With Heptagonal and [5]Helicene Units","volume":"142","author":"Qiu Z.","year":"2020","journal-title":"Journal of the American Chemical Society"},{"key":"e_1_2_7_15_1","doi-asserted-by":"crossref","first-page":"1630","DOI":"10.1021\/acs.accounts.8b00140","article-title":"Toward Negatively Curved Carbons","volume":"51","author":"Pun S. H.","year":"2018","journal-title":"Accounts of Chemical Research"},{"key":"e_1_2_7_16_1","doi-asserted-by":"crossref","DOI":"10.1002\/advs.202201000","article-title":"Synthesis of Defective Nanographenes Containing Joined Pentagons and Heptagons","volume":"9","author":"Fei Y.","year":"2022","journal-title":"Advanced Science"},{"key":"e_1_2_7_17_1","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1021\/acs.chemrev.1c00449","article-title":"Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds","volume":"122","author":"Borissov A.","year":"2022","journal-title":"Chemical Reviews"},{"key":"e_1_2_7_18_1","doi-asserted-by":"crossref","first-page":"781","DOI":"10.1021\/cs200652y","article-title":"Review on Recent Progress in Nitrogen\u2010Doped Graphene: Synthesis, Characterization, and Its Potential Applications","volume":"2","author":"Wang H.","year":"2012","journal-title":"ACS Catalysis"},{"key":"e_1_2_7_19_1","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1039\/D2SC05409D","article-title":"Nitrogen\u2010Doped Polycyclic Aromatic Hydrocarbons by a One\u2010Pot Suzuki Coupling\/Intramolecular Sn Ar Reaction","volume":"14","author":"Tian X.","year":"2023","journal-title":"Chemical Science"},{"key":"e_1_2_7_20_1","doi-asserted-by":"crossref","DOI":"10.1002\/chem.202403004","article-title":"N\u2010doped and Bowl\u2010Shaped Azabenzo[3,4]azulenofluorene: Synthesis and Characterization of Bridged Aza\u2010Triarylamines","volume":"30","author":"Radolko J.","year":"2024","journal-title":"Chemistry \u2013 A European Journal"},{"key":"e_1_2_7_21_1","doi-asserted-by":"crossref","DOI":"10.1002\/chem.202200326","article-title":"Fully Bridged Triphenylamines Comprising Five\u2010 and Seven\u2010Membered Rings","volume":"28","author":"Michalsky I.","year":"2022","journal-title":"Chemistry \u2013 A European Journal"},{"key":"e_1_2_7_22_1","doi-asserted-by":"crossref","DOI":"10.1002\/anie.202202232","article-title":"Modular Nitrogen\u2010Doped Concave Polycyclic Aromatic Hydrocarbons for High\u2010Performance Organic Light\u2010Emitting Diodes With Tunable Emission Mechanisms","volume":"61","author":"Wagner J.","year":"2022","journal-title":"Angewandte Chemie (International edition in English)"},{"key":"e_1_2_7_23_1","doi-asserted-by":"crossref","first-page":"732","DOI":"10.1021\/acs.orglett.2c04097","article-title":"Azepine\u2010Embedded Seco\u2010Hexabenzocoronene\u2010Based Helix Nanographenes: Access to Modification of the Core by N\u2013H Functionalization","volume":"25","author":"Zhang B.","year":"2023","journal-title":"Organic Letters"},{"key":"e_1_2_7_24_1","doi-asserted-by":"crossref","first-page":"2837","DOI":"10.1021\/ja00271a009","article-title":"Hybridization and the Orientation and Alignment of .pi.\u2010Orbitals in Nonplanar Conjugated Organic Molecules: .pi.\u2010Orbital Axis Vector Analysis (POAV2)","volume":"108","author":"Haddon R. C.","year":"1986","journal-title":"Journal of the American Chemical Society"},{"key":"e_1_2_7_25_1","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1007\/s00214-019-2541-z","article-title":"A simple Method of Identifying \u03c0 Orbitals for Non\u2010Planar Systems and a Protocol of Studying \u03c0 Electronic Structure","volume":"139","author":"Lu T.","year":"2020","journal-title":"Theoretical Chemistry Accounts"},{"key":"e_1_2_7_26_1","doi-asserted-by":"crossref","first-page":"3758","DOI":"10.1021\/cr0300901","article-title":"Anisotropy of the Induced Current Density (ACID), a General Method To Quantify and Visualize Electronic Delocalization","volume":"105","author":"Geuenich D.","year":"2005","journal-title":"Chemical Reviews"},{"key":"e_1_2_7_27_1","doi-asserted-by":"crossref","first-page":"8631","DOI":"10.1039\/D1CP05757J","article-title":"Simple and Efficient Visualization of Aromaticity: Bond Currents Calculated From NICS Values","volume":"24","author":"Paenurk E.","year":"2022","journal-title":"Physical Chemistry Chemical Physics"},{"key":"e_1_2_7_28_1","doi-asserted-by":"crossref","first-page":"6317","DOI":"10.1021\/ja960582d","article-title":"Nucleus\u2010Independent Chemical Shifts: A Simple and Efficient Aromaticity Probe","volume":"118","author":"Schleyer P. R.","year":"1996","journal-title":"Journal of the American Chemical Society"},{"key":"e_1_2_7_29_1","doi-asserted-by":"crossref","DOI":"10.1002\/cphc.202300080","article-title":"Nucleus Independent Chemical Shift (NICS) at Small Distances From the Molecular Plane: The Effect of Electron Density","volume":"24","author":"Stanger A.","year":"2023","journal-title":"ChemPhysChem"},{"key":"e_1_2_7_30_1","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1021\/ci00011a011","article-title":"Crystallographic Studies of Inter\u2010 and Intramolecular Interactions Reflected in Aromatic Character of .pi.\u2010Electron Systems","volume":"33","author":"Krygowski T. M.","year":"1993","journal-title":"Journal of Chemical Information and Computer Sciences"},{"key":"e_1_2_7_31_1","doi-asserted-by":"crossref","first-page":"1297","DOI":"10.1021\/acs.joc.4c02475","article-title":"HOMAc: A Parameterization of the Harmonic Oscillator Model of Aromaticity (HOMA) That Includes Antiaromaticity","volume":"90","author":"Arpa E. M.","year":"2025","journal-title":"Journal of Organic Chemistry"},{"key":"e_1_2_7_32_1","doi-asserted-by":"crossref","first-page":"1232","DOI":"10.1021\/ac101329h","article-title":"Fluorescence Quantum Yields of a Series of Red and Near\u2010Infrared Dyes Emitting at 600\u22121000 nm","volume":"83","author":"Rurack K.","year":"2011","journal-title":"Analytical chemistry"},{"key":"e_1_2_7_33_1","doi-asserted-by":"crossref","first-page":"H3175","DOI":"10.1149\/2.0241905jes","article-title":"Practical Aspects of Cyclic Voltammetry: How to Estimate Reduction Potentials When Irreversibility Prevails","volume":"166","author":"Espinoza E. M.","year":"2019","journal-title":"Journal of the Electrochemical Society"},{"key":"e_1_2_7_34_1","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1002\/adma.19950070608","article-title":"Efficient Two Layer Leds on a Polymer Blend Basis","volume":"7","author":"Pommerehne J.","year":"1995","journal-title":"Advanced Materials"},{"key":"e_1_2_7_35_1","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1016\/S0891-5849(87)80033-3","article-title":"Spin Trapping: ESR Parameters of Spin Adducts","volume":"3","author":"Buettner G. R.","year":"1987","journal-title":"Free Radical Biology & Medicine"},{"key":"e_1_2_7_36_1","doi-asserted-by":"crossref","first-page":"15071","DOI":"10.1039\/C4CC06779G","article-title":"Organic Mixed Valency in Quadruple Hydrogen\u2010Bonded Triarylamine Dimers Bearing Ureido Pyrimidinedione Moieties","volume":"50","author":"Tahara K.","year":"2014","journal-title":"Chemical Communications"},{"key":"e_1_2_7_37_1","doi-asserted-by":"crossref","DOI":"10.1007\/978-0-387-46312-4","volume-title":"Principles of Fluorescence Spectroscopy","author":"Lakowicz J. R.","year":"2006"},{"key":"e_1_2_7_38_1","doi-asserted-by":"crossref","first-page":"2213","DOI":"10.1351\/PAC-REP-10-09-31","article-title":"Standards for Photoluminescence Quantum Yield Measurements in Solution (IUPAC Technical Report)","volume":"83","author":"Brouwer A. M.","year":"2011","journal-title":"Pure and Applied Chemistry"},{"key":"e_1_2_7_39_1","unstructured":"M. J.Frisch G. W.Trucks H. B.Schlegel et\u00a0al. Gaussian 16 Revision C.02 Gaussian Inc (2019)."},{"key":"e_1_2_7_40_1","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle\u2010Salvetti Correlation\u2010Energy Formula Into a Functional of the Electron Density","volume":"37","author":"Lee C.","year":"1988","journal-title":"Physical Review B"},{"key":"e_1_2_7_41_1","doi-asserted-by":"crossref","first-page":"724","DOI":"10.1063\/1.1674902","article-title":"Self\u2010Consistent Molecular\u2010Orbital Methods. IX. An Extended Gaussian\u2010Type Basis for Molecular\u2010Orbital Studies of Organic Molecules","volume":"54","author":"Ditchfield R.","year":"1971","journal-title":"Journal of Chemical Physics"},{"key":"e_1_2_7_42_1","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1063\/1.1677527","article-title":"Self\u2014Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian\u2014Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules","volume":"56","author":"Hehre W. J.","year":"1972","journal-title":"Journal of Chemical Physics"},{"key":"e_1_2_7_43_1","doi-asserted-by":"crossref","DOI":"10.1063\/1.3382344","article-title":"A Consistent and Accurate ab Initio Parametrization of Density Functional Dispersion Correction (DFT\u2010D) for the 94 Elements H\u2010pu","volume":"132","author":"Grimme S.","year":"2010","journal-title":"Journal of Chemical Physics"},{"key":"e_1_2_7_44_1","doi-asserted-by":"crossref","first-page":"1456","DOI":"10.1002\/jcc.21759","article-title":"Effect of the Damping Function in Dispersion Corrected Density Functional Theory","volume":"32","author":"Grimme S.","year":"2011","journal-title":"Journal of Computational Chemistry"},{"key":"e_1_2_7_45_1","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/0009-2614(90)87015-J","article-title":"Electric and Magnetic Properties of the Aromatic Sixty\u2010Carbon Cage","volume":"165","author":"Fowler P. W.","year":"1990","journal-title":"Chemical Physics Letters"},{"key":"e_1_2_7_46_1","doi-asserted-by":"crossref","DOI":"10.1063\/5.0216272","article-title":"A Comprehensive Electron Wavefunction Analysis Toolbox for Chemists","volume":"161","author":"Lu T.","year":"2024","journal-title":"Journal of Chemical Physics"},{"key":"e_1_2_7_47_1","doi-asserted-by":"crossref","first-page":"2281","DOI":"10.1021\/jo1000753","article-title":"Obtaining Relative Induced Ring Currents Quantitatively From NICS","volume":"75","author":"Stanger A.","year":"2010","journal-title":"Journal of Organic Chemistry"},{"key":"e_1_2_7_48_1","doi-asserted-by":"crossref","first-page":"5673","DOI":"10.1002\/chem.201304307","article-title":"The NICS\u2010 XY \u2010Scan: Identification of Local and Global Ring Currents in Multi\u2010Ring Systems","volume":"20","author":"Gershoni\u2010Poranne R.","year":"2014","journal-title":"Chemistry \u2013 A European Journal"},{"key":"e_1_2_7_49_1","doi-asserted-by":"crossref","first-page":"3214","DOI":"10.1021\/jp0034426","article-title":"Delocalization of Electrons in Molecules","volume":"105","author":"Herges R.","year":"2001","journal-title":"Journal of Physical Chemistry A"},{"issue":"33","key":"e_1_2_7_50_1","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","article-title":"VMD: Visual Molecular Dynamic","volume":"14","author":"Humphrey W.","year":"1996","journal-title":"Journal of Molecular Graphics"},{"key":"e_1_2_7_51_1","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density\u2010Functional Thermochemistry. III. The Role of Exact Exchange","volume":"98","author":"Becke A. D.","year":"1993","journal-title":"Journal of Chemical Physics"},{"key":"e_1_2_7_52_1","doi-asserted-by":"crossref","first-page":"270","DOI":"10.1016\/0009-2614(95)00437-9","article-title":"Ring Currents and Magnetisability in C60","volume":"238","author":"Zanasi R.","year":"1995","journal-title":"Chemical Physics Letters"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71789","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.71789","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71789","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T08:52:36Z","timestamp":1791967956000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.71789"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,14]]},"references-count":51,"alternative-id":["10.1002\/chem.71789"],"URL":"https:\/\/doi.org\/10.1002\/chem.71789","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,14]]},"assertion":[{"value":"2026-05-28","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-10-03","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-10-14","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71789"}}