{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,15]],"date-time":"2026-07-15T23:56:09Z","timestamp":1784159769894,"version":"3.55.0"},"reference-count":73,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2024,10,28]],"date-time":"2024-10-28T00:00:00Z","timestamp":1730073600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2024,10,28]],"date-time":"2024-10-28T00:00:00Z","timestamp":1730073600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Small"],"published-print":{"date-parts":[[2025,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Atomically precise open\u2010shell graphene fragments, such as extended\n                    <jats:italic>peri<\/jats:italic>\n                    \u2010acenes, hold significant interest for electronics and spintronics. However, their inherent high reactivity poses challenges for synthesis and application. In this study, a novel approach is introduced: the fusion of a zigzag\u2010edged\n                    <jats:italic>peri<\/jats:italic>\n                    \u2010tetracene with an all\u2010armchair\u2010edged hexa\u2010\n                    <jats:italic>peri<\/jats:italic>\n                    \u2010hexabenzocoronene (HBC) via two shared benzene rings to produce a stable open\u2010shell hydrocarbon, named dibenzo\u2010\n                    <jats:italic>peri<\/jats:italic>\n                    \u2010heptacene (DBPH). The DBPH derivative 1 exhibits considerably enhanced stability, with a half\u2010life (\n                    <jats:italic>t<\/jats:italic>\n                    <jats:sub>1\/2<\/jats:sub>\n                    ) of 46 days in toluene solution under ambient conditions. This improved stability is attributed to\n                    <jats:italic>peri<\/jats:italic>\n                    \u2010benzannulation, enhanced aromatic stabilization, and kinetic protection of the reactive sites along the zigzag edges. The structure of\n                    <jats:bold>1<\/jats:bold>\n                    is unequivocally verified through single\u2010crystal X\u2010ray diffraction analysis. With a balanced combination of armchair and zigzag edge structures, derivative\n                    <jats:bold>1<\/jats:bold>\n                    displays a diradical character of 39.2% and a singlet\u2010triplet gap of \u2248\u22123.16 kcal\u00a0mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    . It features a narrow electrochemical energy gap (0.87 eV) and exhibits amphoteric redox behavior. Notably, its dication and dianion states manifest a closed\u2010shell singlet ground state, representing doubly charged structures where a HBC unit is fused with a benzo[\n                    <jats:italic>f<\/jats:italic>\n                    ]tetraphene moiety. This research paves the way for synthesizing novel open\u2010shell graphene fragments with adjustable electronic properties and exceptional stability.\n                  <\/jats:p>","DOI":"10.1002\/smll.202404762","type":"journal-article","created":{"date-parts":[[2024,10,29]],"date-time":"2024-10-29T02:31:14Z","timestamp":1730169074000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Dibenzo\u2010\n                    <i>peri<\/i>\n                    \u2010Heptacene: A Stable Open\u2010Shell Graphene Fragment With a Balanced Combination of Armchair and Zigzag Edge Structures"],"prefix":"10.1002","volume":"21","author":[{"given":"Qing","family":"Jiang","sequence":"first","affiliation":[{"name":"Department of Chemistry National University of Singapore  3 Science Drive 3 Singapore 117543 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