{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,15]],"date-time":"2026-01-15T22:31:49Z","timestamp":1768516309412,"version":"3.49.0"},"reference-count":58,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2021,5,14]],"date-time":"2021-05-14T00:00:00Z","timestamp":1620950400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A set of 3-ethynylaryl coumarin dyes with mono, bithiophenes and the fused variant, thieno [3,2-b] thiophene, as well as an alkylated benzotriazole unit were prepared and tested for dye-sensitized solar cells (DSSCs). For comparison purposes, the variation of the substitution pattern at the coumarin unit was analyzed with the natural product 6,7-dihydroxycoumarin (Esculetin) as well as 5,7-dihydroxycomarin in the case of the bithiophene dye. Crucial steps for extension of the conjugated system involved Sonogashira reaction yielding highly fluorescent molecules. Spectroscopic characterization showed that the extension of conjugation via the alkynyl bridge resulted in a strong red-shift of absorption and emission spectra (in solution) of approximately 73\u201379 nm and 52\u201389 nm, respectively, relative to 6,7-dimethoxy-4-methylcoumarin (\u03bbabs = 341 nm and \u03bbem = 410 nm). Theoretical density functional theory (DFT) calculations show that the Lowest Unoccupied Molecular Orbital (LUMO) is mostly centered in the cyanoacrylic anchor unit, corroborating the high intramolecular charge transfer (ICT) character of the electronic transition. Photovoltaic performance evaluation reveals that the thieno [3,2-b] thiophene unit present in dye 8 leads to the best sensitizer of the set, with a conversion efficiency (\u03b7 = 2.00%), best VOC (367 mV) and second best Jsc (9.28 mA\u00b7cm\u22122), surpassed only by dye 9b (Jsc = 10.19 mA\u00b7cm\u22122). This high photocurrent value can be attributed to increased donor ability of the 5,7-dimethoxy unit when compared to the 6,7 equivalent (9b).<\/jats:p>","DOI":"10.3390\/molecules26102934","type":"journal-article","created":{"date-parts":[[2021,5,14]],"date-time":"2021-05-14T10:54:22Z","timestamp":1620989662000},"page":"2934","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["New 3-Ethynylaryl Coumarin-Based Dyes for DSSC Applications: Synthesis, Spectroscopic Properties, and Theoretical Calculations"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3231-769X","authenticated-orcid":false,"given":"Jo\u00e3o","family":"Sarrato","sequence":"first","affiliation":[{"name":"LAQV-REQUIMTE, Departament of Chemistry, NOVA School of Science and Technology, FCT NOVA, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6251-7994","authenticated-orcid":false,"given":"Ana Lucia","family":"Pinto","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Departament of Chemistry, NOVA School of Science and Technology, FCT NOVA, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6940-5589","authenticated-orcid":false,"given":"Gabriela","family":"Malta","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Departament of Chemistry, NOVA School of Science and Technology, FCT NOVA, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal"}]},{"given":"Eva G.","family":"R\u00f6ck","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Coimbra Chemistry Centre, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"},{"name":"Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1848-1167","authenticated-orcid":false,"given":"Jo\u00e3o","family":"Pina","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Coimbra Chemistry Centre, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1333-9076","authenticated-orcid":false,"given":"Jo\u00e3o Carlos","family":"Lima","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Departament of Chemistry, NOVA School of Science and Technology, FCT NOVA, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0528-1967","authenticated-orcid":false,"given":"A. Jorge","family":"Parola","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Departament of Chemistry, NOVA School of Science and Technology, FCT NOVA, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7312-8596","authenticated-orcid":false,"given":"Paula S.","family":"Branco","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Departament of Chemistry, NOVA School of Science and Technology, FCT NOVA, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2021,5,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1038\/353737a0","article-title":"A Low-Cost, High-Efficiency Solar-Cell Based on Dye-Sensitized Colloidal TiO2 Films","volume":"353","author":"Gratzel","year":"1991","journal-title":"Nature"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"516","DOI":"10.1016\/j.renene.2019.03.146","article-title":"Investigation of semi-transparent dye-sensitized solar cells for fenestration integration","volume":"141","author":"Selvaraj","year":"2019","journal-title":"Renew. 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