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The direct photoirradiation reaction of\n 1<\/jats:bold>\n in the presence of molecular iodine (I\n 2<\/jats:sub>\n ) and propylene oxide preferentially forms\n \n b<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n , but under photoinduced electron\u2010transfer conditions using\n p<\/jats:italic>\n \u2010chloranil as the photosensitizer,\n \n b<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n is generated exclusively. Investigations using nanosecond absorption spectroscopy in conjunction with laser flash photolysis, along with density\u2010functional theory calculations, led to the identification of potential intermediates in these photochemical processes. X\u2010ray crystallographic analysis showed that both\n \n b<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n and\n \n l<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n crystallize in a slipped \u03c0\u2010stacking packing motif. PBEPBE\/6\u201031G* level calculations suggest that crystals of these substances have large charge\u2010transfer integrals (\n t<\/jats:italic>\n ) between neighboring molecules that are \u03c0\u2010stacked along the\n b<\/jats:italic>\n \u2010axis. The\n t<\/jats:italic>\n value for\n \n l<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n (101 meV) is nearly twofold larger than that for\n \n b<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n (54 meV), which is attributed to the existence of more extensive \u03c0\u2010overlap in the former. Based on the Marcus hopping model, theoretical hole mobility along the \u03c0\u2010stacking direction in\n \n l<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n is predicted to be as high as 4.0 cm\n 2<\/jats:sup>\n V\n \u22121<\/jats:sup>\n s\n \u2212<\/jats:sup>\n 1<\/jats:sup>\n . These results suggest that, owing to their excellent charge transport properties, crystals of\n \n b<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n and\n \n l<\/jats:italic>\n \u2010DNT\n <\/jats:bold>\n have the potential of serving as p\u2010type organic semiconductors.\n <\/jats:p>","DOI":"10.1002\/chem.71361","type":"journal-article","created":{"date-parts":[[2026,7,12]],"date-time":"2026-07-12T15:05:36Z","timestamp":1783868736000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["p\u2010Type Organic Semiconductors With an Annulated Thiazole: Photochemical Synthesis and Theoretically High Hole Mobility Predicted From Crystal Structure"],"prefix":"10.1002","author":[{"given":"Masato","family":"Uenaga","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering Osaka Metropolitan University Sakai Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2639-141X","authenticated-orcid":false,"given":"Takuya","family":"Ogaki","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering Osaka Metropolitan University Sakai Osaka Japan"},{"name":"The Research Institute for Molecular Electronic Devices (RIMED) Osaka Metropolitan University Sakai Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7719-0071","authenticated-orcid":false,"given":"Yasunori","family":"Matsui","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering Osaka Metropolitan University Sakai Osaka Japan"},{"name":"The Research Institute for Molecular Electronic Devices (RIMED) Osaka Metropolitan University Sakai Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8161-2177","authenticated-orcid":false,"given":"Hiroshi","family":"Ikeda","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Graduate School of Engineering Osaka Metropolitan University Sakai Osaka Japan"},{"name":"The Research Institute for Molecular Electronic Devices (RIMED) Osaka Metropolitan University Sakai Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,12]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr050966z"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100380z"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.4c11824"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.4c12892"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsapm.4c03902"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201102007"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr500271a"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemmater.1c01972"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/d6cc01367h"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja074841i"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar400282g"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/B403699A"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2jm33039c"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c14775"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c16189"},{"key":"e_1_2_7_17_1","doi-asserted-by":"crossref","unstructured":"D.Bevk 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