{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T19:37:50Z","timestamp":1789587470687,"version":"build-2803163510"},"reference-count":52,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2025,7,23]],"date-time":"2025-07-23T00:00:00Z","timestamp":1753228800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002241","name":"Japan Science and Technology Agency (JST)","doi-asserted-by":"publisher","award":["JPMJS2139"],"award-info":[{"award-number":["JPMJS2139"]}],"id":[{"id":"10.13039\/501100002241","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002241","name":"Japan Science and Technology Agency (JST)","doi-asserted-by":"publisher","award":["JPMJCR2001"],"award-info":[{"award-number":["JPMJCR2001"]}],"id":[{"id":"10.13039\/501100002241","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002241","name":"JST Core Research for Evolutional Science and Technology, Japan","doi-asserted-by":"publisher","award":["JPMJS2139"],"award-info":[{"award-number":["JPMJS2139"]}],"id":[{"id":"10.13039\/501100002241","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002241","name":"JST Core Research for Evolutional Science and Technology, Japan","doi-asserted-by":"publisher","award":["JPMJCR2001"],"award-info":[{"award-number":["JPMJCR2001"]}],"id":[{"id":"10.13039\/501100002241","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this study, we synthesized novel donor\u2013\u03c0\u2013acceptor (D\u2013\u03c0\u2013A) functional dyes bearing a carbonyl-bridged bithiophene as a \u03c0-conjugated spacer and evaluated the absorption and fluorescence properties as well as the photostability. The developed dyes 1-CO\u20133-CO possess an N,N-diphenylaminophenyl electron donor unit and an electron acceptor unit such as a formyl group (1-CO), an (N,N-diethylthiobarbituryl)methylene moiety (2-CO), or a (3-dicyanomethylidene-1-indanon-2-yl)methylene moiety (3-CO). The absorption spectra of 1-CO\u20133-CO in dichloromethane at room temperature showed absorption maxima at 569 nm, 631 nm, and 667 nm, respectively, and the stronger acceptors in 2-CO and 3-CO led to enhancement of the ICT character. In addition, 2-CO and 3-CO had a second absorption band in the visible region, showing panchromatic absorption properties. Electrochemical analyses of the developed dyes revealed that the carbonyl bridging group in the \u03c0-spacer contributes to stabilization of the frontier orbitals such as the highest occupied and lowest unoccupied molecular orbitals (HOMO and LUMO, respectively), in comparison with the referential dyes bearing a dibutylmethylene-bridged bithiophene spacer, 1-CBu2\u20133-CBu2. The HOMO\/LUMO stabilization brought about high photostability in the doped poly(methyl methacrylate) film.<\/jats:p>","DOI":"10.3390\/molecules30153084","type":"journal-article","created":{"date-parts":[[2025,7,23]],"date-time":"2025-07-23T14:22:44Z","timestamp":1753280564000},"page":"3084","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Synthesis and Electronic Properties of Novel Donor\u2013\u03c0\u2013Acceptor-Type Functional Dyes with a Carbonyl-Bridged Bithiophene \u03c0-Spacer"],"prefix":"10.3390","volume":"30","author":[{"given":"Miyu","family":"Ueda","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, 1-1 Gakuen-cho, Naka-ku, Sakai 599-8531, Osaka, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryo","family":"Nagayama","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, 1-1 Gakuen-cho, Naka-ku, Sakai 599-8531, Osaka, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-9703-1222","authenticated-orcid":false,"given":"Masaki","family":"Nagaoka","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, 1-1 Gakuen-cho, Naka-ku, Sakai 599-8531, Osaka, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6187-8664","authenticated-orcid":false,"given":"Naoya","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, 1-1 Gakuen-cho, Naka-ku, Sakai 599-8531, Osaka, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4190-9539","authenticated-orcid":false,"given":"Shintaro","family":"Kodama","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, 1-1 Gakuen-cho, Naka-ku, Sakai 599-8531, Osaka, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4382-6788","authenticated-orcid":false,"given":"Takeshi","family":"Maeda","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, 1-1 Gakuen-cho, Naka-ku, Sakai 599-8531, Osaka, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5310-0062","authenticated-orcid":false,"given":"Shin-ichiro","family":"Kato","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, 1-1 Gakuen-cho, Naka-ku, Sakai 599-8531, Osaka, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4383-748X","authenticated-orcid":false,"given":"Shigeyuki","family":"Yagi","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University, 1-1 Gakuen-cho, Naka-ku, Sakai 599-8531, Osaka, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"e202300262","DOI":"10.1002\/tcr.202300262","article-title":"Design and Photonics of Merocyanine Dyes","volume":"24","author":"Kulinich","year":"2024","journal-title":"Chem. 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