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The effect of the number and position of the alkoxy substituents on the optoelectronic properties has thus been investigated, unveiling p-type semiconducting properties. All molecules displayed a significant colour change upon oxidation, suggesting that these compounds can be used to devise chromogenic materials to engineer electrochromic devices.<\/jats:p>","DOI":"10.1055\/a-1976-0291","type":"journal-article","created":{"date-parts":[[2022,11,9]],"date-time":"2022-11-09T23:57:25Z","timestamp":1668038245000},"page":"240-254","source":"Crossref","is-referenced-by-count":6,"title":["HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes"],"prefix":"10.1055","volume":"4","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9800-3159","authenticated-orcid":false,"given":"Alexandre","family":"Rossignon","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, 5000 Namur, Belgium"},{"name":"School of Chemistry of Cardiff University, Cardiff University, CF10 3\u2009AT Cardiff, United Kingdom"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2446-6860","authenticated-orcid":false,"given":"Beatrice Berionni","family":"Berna","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry, University of Vienna, W\u00e4hringer Stra\u00dfe 38, 1090, Vienna, Austria"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1333-9076","authenticated-orcid":false,"given":"A. 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Sci."},{"key":"ref13","doi-asserted-by":"crossref","first-page":"4740","DOI":"10.1002\/adsc.202100030","volume":"363","author":"C Pezzetta","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"ref14","doi-asserted-by":"crossref","first-page":"429","DOI":"10.1038\/s41467-020-20645-8","volume":"12","author":"Q Ma","year":"2021","journal-title":"Nat. Commun."},{"key":"ref15","doi-asserted-by":"crossref","first-page":"1472","DOI":"10.1021\/ma802755a","volume":"42","author":"C Song","year":"2009","journal-title":"Macromolecules"},{"key":"ref16","doi-asserted-by":"crossref","first-page":"710","DOI":"10.1889\/1.3500568","volume":"41","author":"M Noda","year":"2010","journal-title":"SID Symp. Dig. Tech. Pap."},{"key":"ref17","doi-asserted-by":"crossref","first-page":"22679","DOI":"10.1021\/jp306326e","volume":"116","author":"L Wang","year":"2012","journal-title":"J. Phys. Chem. C"},{"key":"ref18","doi-asserted-by":"crossref","first-page":"2382","DOI":"10.1021\/ol400790d","volume":"15","author":"N Lv","year":"2013","journal-title":"Org. Lett."},{"key":"ref19","doi-asserted-by":"crossref","first-page":"23364","DOI":"10.1021\/acs.jpcc.8b07819","volume":"122","author":"J A Christensen","year":"2018","journal-title":"J. Phys. Chem. C"},{"key":"ref20","doi-asserted-by":"crossref","first-page":"4533","DOI":"10.1016\/S0040-4039(00)80539-0","volume":"29","author":"A Dettling","year":"1988","journal-title":"Tetrahedron Lett."},{"key":"ref21","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1515\/znb-1996-0313","volume":"51","author":"G Frenking","year":"1996","journal-title":"Z. Naturforsch., B: Chem Sci."},{"key":"ref22","doi-asserted-by":"crossref","first-page":"4798","DOI":"10.1021\/ol402172x","volume":"15","author":"S N Keller","year":"2013","journal-title":"Org. Lett."},{"key":"ref23","doi-asserted-by":"crossref","first-page":"5947","DOI":"10.1002\/anie.201509517","volume":"55","author":"D Stassen","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref24","doi-asserted-by":"crossref","first-page":"2714","DOI":"10.1021\/acs.orglett.7b01060","volume":"19","author":"T Kamei","year":"2017","journal-title":"Org. Lett."},{"key":"ref25","doi-asserted-by":"crossref","first-page":"3588","DOI":"10.1055\/s-0037-1611892","volume":"51","author":"A Rossignon","year":"2019","journal-title":"Synthesis"},{"key":"ref26","doi-asserted-by":"crossref","first-page":"2363","DOI":"10.1002\/chem.201604866","volume":"23","author":"T Mileti\u0107","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ref27","doi-asserted-by":"crossref","first-page":"8942","DOI":"10.1002\/anie.201803282","volume":"57","author":"A Berezin","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref28","doi-asserted-by":"crossref","first-page":"13787","DOI":"10.1021\/acs.joc.8b02076","volume":"83","author":"A Sciutto","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref29","doi-asserted-by":"crossref","first-page":"6335","DOI":"10.1039\/D2SC01038K","volume":"13","author":"C Valentini","year":"2022","journal-title":"Chem. Sci."},{"key":"ref30","doi-asserted-by":"crossref","first-page":"60473","DOI":"10.1039\/C4RA10652K","volume":"4","author":"L Dobelmann","year":"2014","journal-title":"RSC Adv."},{"key":"ref31","doi-asserted-by":"crossref","first-page":"4283","DOI":"10.1021\/acs.orglett.0c01331","volume":"22","author":"L \u0110or\u0111evi\u0107","year":"2020","journal-title":"Org. Lett."},{"key":"ref32","doi-asserted-by":"crossref","first-page":"e202101166","DOI":"10.1002\/ejoc.202101166","volume":"2022","author":"J Fletcher-Charles","year":"2022","journal-title":"Eur. J. Org. 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