{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T11:57:27Z","timestamp":1790251047203,"version":"4.1.0"},"reference-count":75,"publisher":"Wiley","issue":"39","license":[{"start":{"date-parts":[[2017,8,18]],"date-time":"2017-08-18T00:00:00Z","timestamp":1503014400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2017,9,18]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Reaction of an N\u2010heterocyclic carbene (NHC)\u2013borenium ion with 9,10\u2010distyrylanthracene forms four B\u2212C bonds through two selective, tandem hydroboration\u2013electrophilic C\u2212H borylations to yield an isolable, crystallographically characterizable polycyclic diborenium ion as its [NTf<jats:sub>2<\/jats:sub>]<jats:sup>\u2212<\/jats:sup> salt (<jats:bold>1<\/jats:bold>). Dehydrogenation of <jats:bold>1<\/jats:bold> with TEMPO radical followed by acidic workup yields a 3,9\u2010diboraperylene as its corresponding borinic acid (<jats:bold>2<\/jats:bold>). This sequence can be performed in one pot to allow the facile, metal\u2010free conversion of an alkene into a small molecule containing a boron\u2010doped graphene substructure. Doubly boron\u2010doped perylene <jats:bold>2<\/jats:bold> exhibits visible range absorbance and fluorescence in chloroform solution (<jats:italic>\u03a6<\/jats:italic>=0.63) and undergoes two reversible one\u2010electron reductions at moderate potentials of \u22121.30 and \u22121.64\u2005eV vs. ferrocenium\/ferrocene in DMSO. Despite sterically accessible boron centers and facile electrochemical reductions, compound <jats:bold>2<\/jats:bold> is air\u2010, moisture\u2010, and silica gel\u2010stable.<\/jats:p>","DOI":"10.1002\/anie.201706346","type":"journal-article","created":{"date-parts":[[2017,7,25]],"date-time":"2017-07-25T11:06:37Z","timestamp":1500980797000},"page":"11846-11850","source":"Crossref","is-referenced-by-count":76,"title":["Synthesis of a Doubly Boron\u2010Doped Perylene through NHC\u2010Borenium Hydroboration\/C\u2212H Borylation\/Dehydrogenation"],"prefix":"10.1002","volume":"56","author":[{"given":"Jeffrey M.","family":"Farrell","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Organische Chemie Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Schmidt","sequence":"additional","affiliation":[{"name":"Center for Nanosystems Chemistry (CNC) Universit\u00e4t W\u00fcrzburg  Theodor-Boveri-Weg 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vincenzo","family":"Grande","sequence":"additional","affiliation":[{"name":"Center for Nanosystems Chemistry (CNC) Universit\u00e4t W\u00fcrzburg  Theodor-Boveri-Weg 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7245-0471","authenticated-orcid":false,"given":"Frank","family":"W\u00fcrthner","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische Chemie Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"},{"name":"Center for Nanosystems Chemistry (CNC) Universit\u00e4t W\u00fcrzburg  Theodor-Boveri-Weg 97074 W\u00fcrzburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,8,18]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1102896"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900070d"},{"key":"e_1_2_2_4_1","unstructured":"\u00a0"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902532"},{"key":"e_1_2_2_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200902532"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102326"},{"key":"e_1_2_2_6_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102326"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309746"},{"key":"e_1_2_2_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309746"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00183H"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00076"},{"key":"e_1_2_2_10_1","unstructured":"\u00a0"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC00175G"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC04245G"},{"key":"e_1_2_2_13_1","unstructured":"\u00a0"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100026f"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900401a"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901217"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901217"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608324"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201608324"},{"key":"e_1_2_2_19_1","unstructured":"\u00a0"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5TA10599D"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00991"},{"key":"e_1_2_2_22_1","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/om8005068"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201001922"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206699"},{"key":"e_1_2_2_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206699"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3036042"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502977"},{"key":"e_1_2_2_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201502977"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC07208E"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00800"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b02303"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201701591"},{"key":"e_1_2_2_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201701591"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b03167"},{"key":"e_1_2_2_33_1","unstructured":"Recently on-surface syntheses have been described:"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b02523"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms9098"},{"key":"e_1_2_2_36_1","unstructured":"\u00a0"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201001402"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00188"},{"key":"e_1_2_2_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102717"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102717"},{"key":"e_1_2_2_40_1","unstructured":"\u00a0"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00069a004"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500402"},{"key":"e_1_2_2_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500402"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200133c"},{"key":"e_1_2_2_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja305061c"},{"key":"e_1_2_2_45_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0031-1291147"},{"key":"e_1_2_2_46_1","unstructured":"\u00a0"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja905369n"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja208093c"},{"key":"e_1_2_2_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500198"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500198"},{"key":"e_1_2_2_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja407458k"},{"key":"e_1_2_2_51_1","unstructured":"\u00a0"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/om900476g"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja307995f"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC03675A"},{"key":"e_1_2_2_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00627"},{"key":"e_1_2_2_56_1","unstructured":"A quasi-reversible speciation change is observed for2under strongly basic conditions (see the Supporting Information)."},{"key":"e_1_2_2_57_1","unstructured":"\u00a0"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja506980p"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502678"},{"key":"e_1_2_2_59_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201502678"},{"key":"e_1_2_2_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6QO00047A"},{"key":"e_1_2_2_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00851a031"},{"key":"e_1_2_2_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja211944q"},{"key":"e_1_2_2_63_1","unstructured":"CCDC\u20051554912\u2005(1) and 1554913\u2005(2) contain the supplementary crystallographic data for this paper. These data are provided free of charge byThe Cambridge Crystallographic Data Centre."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201706346","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201706346","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,10]],"date-time":"2023-09-10T02:29:28Z","timestamp":1694312968000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201706346"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,8,18]]},"references-count":75,"journal-issue":{"issue":"39","published-print":{"date-parts":[[2017,9,18]]}},"alternative-id":["10.1002\/anie.201706346"],"URL":"https:\/\/doi.org\/10.1002\/anie.201706346","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,8,18]]}}}