{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T06:10:13Z","timestamp":1789193413552,"version":"build-2803163510"},"reference-count":45,"publisher":"Wiley","issue":"34","license":[{"start":{"date-parts":[[2026,5,27]],"date-time":"2026-05-27T00:00:00Z","timestamp":1779840000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,5,27]],"date-time":"2026-05-27T00:00:00Z","timestamp":1779840000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/V027735\/1"],"award-info":[{"award-number":["EP\/V027735\/1"]}],"id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2026,9,11]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Dithieno[3,2\u2010\n                    <jats:italic>b<\/jats:italic>\n                    :2\u2018,3\u2019\u2010\n                    <jats:italic>e<\/jats:italic>\n                    ]pyridine (\n                    <jats:bold>DTP<\/jats:bold>\n                    ) is a heterocycle consisting of a central pyridine ring fused with two thiophene rings and can be regarded as a thiophene\u2010based analogue of the classic\n                    <jats:italic>N<\/jats:italic>\n                    \u2010heterocycle acridine. Unlike acridine\u2010based dyes, the fundamental chemistry of\n                    <jats:bold>DTP<\/jats:bold>\n                    has received relatively little attention. Here, we report the straightforward synthesis of a library of\n                    <jats:bold>DTP<\/jats:bold>\n                    molecules and an investigation of their electronic properties using UV\/vis absorbance and emission spectroscopy supported by computational insights, with particular focus on the influence of protonation and methylation of the central N atom on their properties. While the absorbance of the\n                    <jats:bold>DTPs<\/jats:bold>\n                    studied was confined to ultraviolet wavelengths, protonation or\n                    <jats:italic>N<\/jats:italic>\n                    \u2010methylation of the pyridine group led to significant visible light absorption, which was exploited for the visible light photosensitisation of oxygen.\n                  <\/jats:p>","DOI":"10.1002\/chem.71186","type":"journal-article","created":{"date-parts":[[2026,5,27]],"date-time":"2026-05-27T08:15:13Z","timestamp":1779869713000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Single\u2010Step Synthesis of Dithieno[3,2\u2010\n                    <i>b<\/i>\n                    :2\u2032,3\u2032\u2010\n                    <i>e<\/i>\n                    ]Pyridines and Their Acid\u2010Dependent Optical and Photosensitising Properties"],"prefix":"10.1002","volume":"32","author":[{"given":"Dominic","family":"Taylor","sequence":"first","affiliation":[{"name":"EastCHEM School of Chemistry University of Edinburgh  Edinburgh UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthew","family":"Wallace","sequence":"additional","affiliation":[{"name":"EastCHEM School of Chemistry University of Edinburgh  Edinburgh UK"},{"name":"School of Engineering and Physical Sciences Heriot\u2010Watt University  Edinburgh UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Leonardo","family":"Amicosante","sequence":"additional","affiliation":[{"name":"School of Engineering and Physical Sciences Heriot\u2010Watt University  Edinburgh UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gary S.","family":"Nichol","sequence":"additional","affiliation":[{"name":"EastCHEM School of Chemistry University of Edinburgh  Edinburgh UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7831-012X","authenticated-orcid":false,"given":"Scott J.","family":"Dalgarno","sequence":"additional","affiliation":[{"name":"School of Engineering and Physical Sciences Heriot\u2010Watt University  Edinburgh UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Filipe","family":"Vilela","sequence":"additional","affiliation":[{"name":"School of Engineering and Physical Sciences Heriot\u2010Watt University  Edinburgh UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0142-2809","authenticated-orcid":false,"given":"Iain A.","family":"Wright","sequence":"additional","affiliation":[{"name":"EastCHEM School of Chemistry University of Edinburgh  Edinburgh UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6027-261X","authenticated-orcid":false,"given":"Neil B.","family":"McKeown","sequence":"additional","affiliation":[{"name":"EastCHEM School of Chemistry University of Edinburgh  Edinburgh UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,5,27]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsapm.4c03585"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2024.112097"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41427\u2010019\u20100163\u20105"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.3390\/ma15217560"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4TC05497K"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC02990C"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202403388"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)73842-1"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01240"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ma035329u"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ma902164q"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/pola.24887"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01235"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26061788"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570330103"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)00681-9"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/B205227J"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201600802"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2019.05.020"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.6.112"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3QO00684K"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c04897"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201300753"},{"key":"e_1_2_7_25_1","unstructured":"Deposition numbers 2503850 (forPh\u2010DTP) 2503851 (forF5\u2010DTP) 2503852 (forpOMe\u2010DTP) 2503853 (forTh\u2010DTP) and 2503854 (for[Ph\u2010DTP\u2010Me+][I\u2212]) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2052520616003954"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4TA01009D"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01025a059"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00371a065"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(00)82045-7"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4RA05540C"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2BM00780K"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41428-024-00961-2"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/adhm.202102015"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202008708"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2021.134327"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5c01003"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1080\/14686996.2021.1967698"},{"key":"e_1_2_7_39_1","first-page":"339","article-title":"A Short History of ShelX","volume":"64","author":"Sheldrick G. M.","year":"2008","journal-title":"Acta Crystallographica Section A"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889808042726"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053273314022207"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jchemed.4c01241"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397919508011446"},{"key":"e_1_2_7_44_1","unstructured":"Sigma\u2010Aldrich. Physical properties of Solvents https:\/\/www.sigmaaldrich.com\/deepweb\/assets\/sigmaaldrich\/marketing\/global\/documents\/614\/456\/labbasics_pg144.pdf accessed October2025."},{"key":"e_1_2_7_45_1","unstructured":"M. J.Frisch G. W.Trucks H. B.Schlegel et\u00a0al. \u201cGaussian 16 Revision A.03 \u201d (Gaussian Inc. 2016)."},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205735"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71186","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.71186","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71186","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T05:15:33Z","timestamp":1789190133000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.71186"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,5,27]]},"references-count":45,"journal-issue":{"issue":"34","published-print":{"date-parts":[[2026,9,11]]}},"alternative-id":["10.1002\/chem.71186"],"URL":"https:\/\/doi.org\/10.1002\/chem.71186","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,5,27]]},"assertion":[{"value":"2026-03-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-05-15","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-05-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71186"}}