{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T11:58:19Z","timestamp":1791892699235,"version":"4.3.4"},"reference-count":70,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T00:00:00Z","timestamp":1791849600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T00:00:00Z","timestamp":1791849600000},"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                    Replacement of benzenoid subunits by isoelectronic heteroaromatic motifs, N\u2010doping, and \u03c0\u2010extension provide complementary strategies for modulating the electronic structure and physical properties of polycyclic aromatic \u03c0\u2010systems. Ullazine (indolizino[6,5,4,3\u2010aij]quinoline) can be regarded as a \u03c0\u2010isoelectronic heteroaromatic analogue of pyrene in which one six\u2010membered benzenoid ring is replaced by a five\u2010membered pyrrolic ring. Ullazine derivatives are of considerable interest in materials chemistry because this structural modification substantially alters their electronic properties relative to pyrene. Herein, we report peroullazine (\n                    <jats:bold>PU<\/jats:bold>\n                    ), a longitudinally \u03c0\u2010extended ullazine analogue of peropyrene, together with the pyridinic azaperoullazines\n                    <jats:bold>7\u2010APU<\/jats:bold>\n                    and\n                    <jats:bold>8\u2010APU<\/jats:bold>\n                    . Their synthesis combines Pd\u2010catalyzed cross\u2010coupling with two\u2010 and fourfold alkyne benzannulation. Replacing a pyrene substructure with an ullazine unit renders these \u03c0\u2010systems markedly more electron\u2010rich than the corresponding peropyrene and azaperopyrene counterparts, as reflected in substantially lower oxidation potentials. Most strikingly, this pyrene\u2010to\u2010ullazine replacement produces strongly red\u2010shifted optical transitions and optical gaps approaching those of considerably more \u03c0\u2010extended teropyrenes, despite the peropyrene\u2010sized \u03c0\u2010system. Pyridinic nitrogen incorporation further produces pronounced position\u2010dependent effects, with substitution at the 7\u2010position exerting a substantially stronger influence than substitution at the 8\u2010position on the optical, electrochemical, and protonation responses.\n                  <\/jats:p>","DOI":"10.1002\/chem.71799","type":"journal-article","created":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T11:04:44Z","timestamp":1791889484000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Peroullazines: Synthesis, Structure, and Optoelectronic Properties"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0007-1414-0169","authenticated-orcid":false,"given":"Ricardo","family":"Molenda","sequence":"first","affiliation":[{"name":"Institute of Chemistry University of Rostock  Rostock Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-6704-7619","authenticated-orcid":false,"given":"Ha Minh","family":"Tuan","sequence":"additional","affiliation":[{"name":"Institute of Chemistry University of Rostock  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":[[2026,10,13]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00183H"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00322"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100428a"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19830660724"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8TC03573C"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/aenm.201200701"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201800030"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)72628\u20101"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201604741"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202100686"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202404849"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6c01154"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19430760504"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201804453"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp4051116"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1139\/cjc\u20102016\u20100569"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b06848"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201903413"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c02985"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202503136"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo011133l"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201914900"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205007"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201701347"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c00386"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c01772"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/D6CC00401F"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00554"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c00777"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202400637"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc202306020"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5RA03527A"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4OB00091A"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules29092159"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6c02030"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201907972"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201704694"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c02394"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c01622"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02149F"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo025962y"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400220"},{"key":"e_1_2_7_44_1","doi-asserted-by":"crossref","first-page":"5198","DOI":"10.1002\/chem.201505052","article-title":"Z\u2010Shaped Pyrrolo[3,2\u2010b]pyrroles and Their Transformation Into \u03c0\u2010Expanded Indolo[3,2\u2010b]indoles","volume":"22","author":"St\u0119\u017cycki R.","year":"2016","journal-title":"Chemistry\u2014A European Journal"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8QO00389K"},{"key":"e_1_2_7_46_1","unstructured":"Deposition Numbers 2576374 (PU) and 2576375 (8\u2010APU) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service. For7\u2010APU no deposition number is available owing to the limited quality of the crystallographic data. The crystal diffracted only weakly and was twinned; the pyridinic nitrogen is positionally disordered over two sites with a major\u2010site occupancy of 76% and all atoms were refined isotropically."},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1139\/cjc\u20102016\u20100466"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201702594"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0QO00033G"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202100333"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214\u2010019\u20102541\u2010z"},{"key":"e_1_2_7_52_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. V. 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