{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T03:02:23Z","timestamp":1785898943900,"version":"3.56.0"},"reference-count":46,"publisher":"Wiley","issue":"31","license":[{"start":{"date-parts":[[2023,3,17]],"date-time":"2023-03-17T00:00:00Z","timestamp":1679011200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP21H05491"],"award-info":[{"award-number":["JP21H05491"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["20K21196"],"award-info":[{"award-number":["20K21196"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["21H04685"],"award-info":[{"award-number":["21H04685"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Small"],"published-print":{"date-parts":[[2023,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Precisely controlled molecular assemblies often display intriguing morphologies and\/or functions arising from their structures. The application of the concept of the self\u2010assembly for controlling the aggregation of nanographenes (NGs) is challenging. The title NGs are those carrying both long alkyl chains and tris(phenylisoxazolyl)benzene (TPIB) on the edge. The former group secures the affinity of NGs for organic solvents, and the latter group drives the 1D arrangement of NGs through the interactions between the TPIB units. The concentration\u2010dependent and temperature variable <jats:sup>1<\/jats:sup>H NMR, UV\u2013vis, and PL spectra demonstrate the aggregation of NGs in 1,2\u2010dichloroethane, and the aggregation is controllable by the regulation of the solvent polarity. AFM images give the stacked structures of the NGs, and these aggregates turn out to be network polymeric structures at a high concentration. These observations demonstrate that the synergy of the face\u2010to\u2010face interactions between the surfaces and the interactions between the TPIB units are effective for controlling the self\u2010assembly of the NGs.<\/jats:p>","DOI":"10.1002\/smll.202207475","type":"journal-article","created":{"date-parts":[[2023,3,17]],"date-time":"2023-03-17T11:04:40Z","timestamp":1679051080000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Substituent\u2010Induced Supramolecular Aggregates of Edge Functionalized Nanographenes"],"prefix":"10.1002","volume":"19","author":[{"given":"Haruka","family":"Moriguchi","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Advanced Science and Engineering Hiroshima University  1\u20103\u20101 Kagamiyama, Higashi\u2010Hiroshima Hiroshima 739\u20138526 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2108-4296","authenticated-orcid":false,"given":"Ryo","family":"Sekiya","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Advanced Science and Engineering Hiroshima University  1\u20103\u20101 Kagamiyama, Higashi\u2010Hiroshima Hiroshima 739\u20138526 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0945-2893","authenticated-orcid":false,"given":"Takeharu","family":"Haino","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Advanced Science and Engineering Hiroshima University  1\u20103\u20101 Kagamiyama, Higashi\u2010Hiroshima Hiroshima 739\u20138526 Japan"},{"name":"International Institute for Sustainability with Knotted Chiral Meta Matter (SKCM <sup>2<\/sup>) Hiroshima University  2\u2013313 Kagamiyama, Higashi\u2010Hiroshima Hiroshima 739\u20138527 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,3,17]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1205962"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1134441"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701139"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1107749"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja020984n"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202206729"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202200120"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202114290"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja052645a"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja302574b"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202209806"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00660"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800417"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603370"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.200031"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB00492A"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC02571J"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c03005"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmat1849"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1102896"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202101438"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/smll.202200919"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/smll.202207227"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205514"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202102741"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201201930"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201600058"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202108645"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/ppsc.201300252"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202200291"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.202003213"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201705791"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202211365"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202101992"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201713299"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201311248"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201504963"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.20200381"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9RA07528C"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB01277K"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.202200465"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic00068a012"},{"key":"e_1_2_8_43_1","unstructured":"G. W. T. M. J.Frisch H. B.Schlegel G. E.Scuseria M. A.Robb J. R.Cheeseman G.Scalmani V.Barone G. A.Petersson H.Nakatsuji X.Li M.Caricato A. V.Marenich J.Bloino B. G.Janesko R.Gomperts B.Mennucci H. P.Hratchian J. V.Ortiz A. F.Izmaylov J. L.Sonnenberg D.Williams\u2010Young F.Ding F.Lipparini F.Egidi J.Goings B.Peng A.Petrone T.Henderson D.Ranasinghe V. G.Zakrzewski et\u00a0al. Gaussian Inc. Wallingford CT 2016 Gaussian 16 Revision C.01."},{"key":"e_1_2_8_44_1","unstructured":"Our previous computational calculations ref. [41] demonstrated that carboxy groups on the edge distort the edge and that the conversion of the carboxy groups to the five\u2010membered imide rings does not significantly change the edge structure. Hence the non\u2010coplanar orientation of the TPIB unit is expected to be adopted irrespective of the five\u2010membered imides. Indeed a DFT calculation of a model edge structure that carries one TPIB unit and four carboxy groups on the edge gave a similar structure (FigureS30 Supporting Information)."},{"key":"e_1_2_8_45_1","unstructured":"We also conducted scanning electron microscope (SEM) measurements ofNG1a. SEM gave an image of amorphous ofNG1a(FigureS35 Supporting Information). No obvious nanostructures were found."},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1080\/15583724.2010.493255"}],"container-title":["Small"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/smll.202207475","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/smll.202207475","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/smll.202207475","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,17]],"date-time":"2023-08-17T06:27:46Z","timestamp":1692253666000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/smll.202207475"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,17]]},"references-count":46,"journal-issue":{"issue":"31","published-print":{"date-parts":[[2023,8]]}},"alternative-id":["10.1002\/smll.202207475"],"URL":"https:\/\/doi.org\/10.1002\/smll.202207475","archive":["Portico"],"relation":{},"ISSN":["1613-6810","1613-6829"],"issn-type":[{"value":"1613-6810","type":"print"},{"value":"1613-6829","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,3,17]]},"assertion":[{"value":"2022-11-30","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-03-17","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"2207475"}}