{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T05:51:18Z","timestamp":1791352278473,"version":"4.3.1"},"reference-count":27,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:00:00Z","timestamp":1791244800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:00:00Z","timestamp":1791244800000},"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                    Postsynthetic annulative \u03c0\u2010extension offers a direct route to reshape the \u03c0\u2010surface of subphthalocyanines (SubPcs) without exposing elaborate phthalonitrile precursors to the harsh cyclotrimerization conditions. Here, a\n                    <jats:italic>\u03b2,\u03b2<\/jats:italic>\n                    \u2010diiodo SubPc undergoes twofold Suzuki\u2013Miyaura cross\u2010coupling with biphenyl\u20102,2\u2032\u2010diboronic acid or racemic [1,1\u2032\u2010binaphthalene]\u20102,2\u2032\u2010diboronic acid to afford triphenylene\u2010fused\n                    <jats:bold>1<\/jats:bold>\n                    and [5]helicene\u2010fused\n                    <jats:bold>2<\/jats:bold>\n                    in 40% and 43% yield, respectively. Annulation redshifts the Q\u2010band absorption and fluorescence maxima by up to 30 and 34\u00a0nm and increases the fluorescence quantum yield in CHCl\n                    <jats:sub>3<\/jats:sub>\n                    from 0.25 for parent SubPc 0 to 0.36 and 0.45 for\n                    <jats:bold>1<\/jats:bold>\n                    and\n                    <jats:bold>2<\/jats:bold>\n                    . Electrochemistry and density functional theory indicate only modest changes in the frontier\u2010orbital energies, with the low\u2010energy electronic structure remaining largely SubPc\u2010centered. Localized concentration\u2010 and temperature\u2010dependent\n                    <jats:sup>1<\/jats:sup>\n                    H NMR shifts are consistent with lateral association involving the annulated polycyclic aromatic surface. Compound\n                    <jats:bold>2<\/jats:bold>\n                    is configurationally labile, but its enantiomers can be resolved by chiral HPLC and display mirror\u2010image circular dichroism across the visible region before racemizing over several hours in dilute solution.\n                  <\/jats:p>","DOI":"10.1002\/chem.71744","type":"journal-article","created":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T05:31:06Z","timestamp":1791351066000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Postsynthetic Annulative \u03c0\u2010Extension of Subphthalocyanines: Triphenylene\u2010 and [5]Helicene\u2010Fused Chromophores"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1873-0293","authenticated-orcid":false,"given":"Jos\u00e9","family":"Garc\u00eda\u2010Calvo","sequence":"first","affiliation":[{"name":"Departamento De Qu\u00edmica Org\u00e1nica Universidad Aut\u00f3noma de Madrid  Madrid Spain"},{"name":"Institute For Advanced Research in Chemical Sciences (IAdChem) Universidad Aut\u00f3noma de Madrid  Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria","family":"Lahoz","sequence":"additional","affiliation":[{"name":"Departamento De Qu\u00edmica Org\u00e1nica Universidad Aut\u00f3noma de Madrid  Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paula","family":"de la Rubia","sequence":"additional","affiliation":[{"name":"Departamento De Qu\u00edmica Org\u00e1nica Universidad Aut\u00f3noma de Madrid  Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9335-6935","authenticated-orcid":false,"given":"Tom\u00e1s","family":"Torres","sequence":"additional","affiliation":[{"name":"Departamento De Qu\u00edmica Org\u00e1nica Universidad Aut\u00f3noma de Madrid  Madrid Spain"},{"name":"Institute For Advanced Research in Chemical Sciences (IAdChem) Universidad Aut\u00f3noma de Madrid  Madrid Spain"},{"name":"Instituto Madrile\u00f1o de Estudios Avanzados En Nanociencia (IMDEA Nanoscience)  Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7176-7215","authenticated-orcid":false,"given":"M. V.","family":"Martinez\u2010Diaz","sequence":"additional","affiliation":[{"name":"Departamento De Qu\u00edmica Org\u00e1nica Universidad Aut\u00f3noma de Madrid  Madrid Spain"},{"name":"Institute For Advanced Research in Chemical Sciences (IAdChem) Universidad Aut\u00f3noma de Madrid  Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,6]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CS00280A"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0ME00150C"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.trechm.2023.02.003"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20102007\u20101000823"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200801250"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1142\/S1088424625500427"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5c02679"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300709"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsaem.8b01918"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmaterialslett.9b00221"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00944"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmaterialslett.2c01132"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)01056\u2010X"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c06377"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC01069D"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC03426K"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep28026"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.71412"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201801190"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201500074"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19971300718"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c07291"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206111"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4ME00070F"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.202001099"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja950774t"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01461"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71744","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.71744","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71744","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T05:31:07Z","timestamp":1791351067000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.71744"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,6]]},"references-count":27,"alternative-id":["10.1002\/chem.71744"],"URL":"https:\/\/doi.org\/10.1002\/chem.71744","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,6]]},"assertion":[{"value":"2026-08-06","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-03","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-10-06","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71744"}}