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Tuning of the optical band gap was achieved through \u03c0\u2010extension by annulation of a benzene or tropone moiety to the thiophene, oxidation, change of the heteroatom or by attachment of a donor substituent to the thiophene core. The resulting compounds display intense colors covering the entire visible spectrum. We identified structure\u2010property relationships and their impact on the HOMO and LUMO levels. Additionally, these materials change color upon reduction and according to in\u2005situ ultraviolet\u2010visible\u2010near infrared (UV\u2010vis\u2010NIR) and electron paramagnetic resonance (EPR) spectro\u2010electrochemistry, they are promising electrochromes with cathodic color changes. Seven different electrochromic devices were constructed which all displayed a change in color upon reduction, demonstrating the potential of these new dyes in for example tintable glass.<\/jats:p>","DOI":"10.1002\/chem.202203862","type":"journal-article","created":{"date-parts":[[2023,2,15]],"date-time":"2023-02-15T03:35:35Z","timestamp":1676432135000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Heterophenoquinones: Tuning Optoelectronics and Electrochromicity"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7053-5815","authenticated-orcid":false,"given":"Willi M.","family":"Amberg","sequence":"first","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sebastian N.","family":"Intorp","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7490-617X","authenticated-orcid":false,"given":"Evgenia","family":"Dmitrieva","sequence":"additional","affiliation":[{"name":"Center of Spectroelectrochemistry Leibniz Institute for Solid State and Materials Research (IFW) Dresden  Helmholtzstra\u00dfe 20 01069 Dresden Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7596-0378","authenticated-orcid":false,"given":"Alexey A.","family":"Popov","sequence":"additional","affiliation":[{"name":"Center of Spectroelectrochemistry Leibniz Institute for Solid State and Materials Research (IFW) Dresden  Helmholtzstra\u00dfe 20 01069 Dresden Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Frank","family":"Rominger","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0998-693X","authenticated-orcid":false,"given":"Jan","family":"Freudenberg","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9369-5387","authenticated-orcid":false,"given":"Uwe H. 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