{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,25]],"date-time":"2025-12-25T13:06:45Z","timestamp":1766668005455,"version":"build-2065373602"},"reference-count":34,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2024,5,9]],"date-time":"2024-05-09T00:00:00Z","timestamp":1715212800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004040","name":"Research Council of KU Leuven","doi-asserted-by":"publisher","award":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"],"award-info":[{"award-number":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"]}],"id":[{"id":"10.13039\/501100004040","id-type":"DOI","asserted-by":"publisher"}]},{"name":"China Scholarship Council","award":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"],"award-info":[{"award-number":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"]}]},{"name":"Research Foundation\u2014Flanders (FWO)","award":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"],"award-info":[{"award-number":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"]}]},{"name":"Hercules Foundation of the Flemish Government","award":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"],"award-info":[{"award-number":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"]}]},{"name":"Hercules","award":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"],"award-info":[{"award-number":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"]}]},{"name":"Hercules Foundation","award":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"],"award-info":[{"award-number":["C14\/19\/78","C14\/19\/079","PDM\/20\/091","201706920044","1SC4719N","20100225-7","I002720N","G0D6221N","AKUL\/09\/0035"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Methyl 4-(1,3a,6a-triazapentalen-3-yl)benzoate (TAP1) shows interesting properties as a small molecule fluorophore. In the search for post-functionalization methods, palladium-catalyzed arylation reactions were demonstrated. Direct CH arylation reactions of TAP1 with various aryl halides resulted in 3,6-diaryltriazapentalenes TAP4, although mostly in poor yields. Bromination of TAP1 followed by Suzuki coupling, on the other hand, requires a more delicate procedure, but gave arylated products with the same regiochemistry (TAP4) in moderate to good yields. The structure of 6-phenyltriazapentalene TAP4a was confirmed by crystallographic analysis. In addition, the effect of the C6 arylation on the fluorescent properties of 3-aryl-1,3a,6a-triazapentalenes was studied in dichloromethane at room temperature and in 2-methyltetrahydrofuran at 77 K, while the photophysical properties of two saponified derivatives were measured in acetonitrile.<\/jats:p>","DOI":"10.3390\/molecules29102229","type":"journal-article","created":{"date-parts":[[2024,5,10]],"date-time":"2024-05-10T03:21:04Z","timestamp":1715311264000},"page":"2229","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Palladium-Catalyzed Arylations towards 3,6-Diaryl-1,3a,6a-triazapentalenes and Evaluation of Their Fluorescence Properties"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4425-5465","authenticated-orcid":false,"given":"Yingchun","family":"Wang","sequence":"first","affiliation":[{"name":"Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8272-0292","authenticated-orcid":false,"given":"Tomas","family":"Opsomer","sequence":"additional","affiliation":[{"name":"Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3442-0316","authenticated-orcid":false,"given":"Flip","family":"de Jong","sequence":"additional","affiliation":[{"name":"Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8872-1360","authenticated-orcid":false,"given":"Davy","family":"Verhaeghe","sequence":"additional","affiliation":[{"name":"Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-4761-4296","authenticated-orcid":false,"given":"Maarten","family":"Mulier","sequence":"additional","affiliation":[{"name":"Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2186-5209","authenticated-orcid":false,"given":"Luc","family":"Van Meervelt","sequence":"additional","affiliation":[{"name":"Biochemistry, Molecular and Structural Biology, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mark","family":"Van der Auweraer","sequence":"additional","affiliation":[{"name":"Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9597-0629","authenticated-orcid":false,"given":"Wim","family":"Dehaen","sequence":"additional","affiliation":[{"name":"Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,5,9]]},"reference":[{"key":"ref_1","unstructured":"Wang, Y., Opsomer, T., and Dehaen, W. 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