{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T10:57:14Z","timestamp":1762081034461,"version":"build-2065373602"},"reference-count":67,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2022,12,14]],"date-time":"2022-12-14T00:00:00Z","timestamp":1670976000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["PTDC\/QUI-QFI\/2870\/2020","CEECINST\/00069\/2021","2022.13031.BD","UIDB\/00081\/2020","UIDB\/05748\/2020","LA\/P\/0056\/2020"],"award-info":[{"award-number":["PTDC\/QUI-QFI\/2870\/2020","CEECINST\/00069\/2021","2022.13031.BD","UIDB\/00081\/2020","UIDB\/05748\/2020","LA\/P\/0056\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"R&amp;D Units CIQUP","doi-asserted-by":"publisher","award":["PTDC\/QUI-QFI\/2870\/2020","CEECINST\/00069\/2021","2022.13031.BD","UIDB\/00081\/2020","UIDB\/05748\/2020","LA\/P\/0056\/2020"],"award-info":[{"award-number":["PTDC\/QUI-QFI\/2870\/2020","CEECINST\/00069\/2021","2022.13031.BD","UIDB\/00081\/2020","UIDB\/05748\/2020","LA\/P\/0056\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"GreenUPOrto","doi-asserted-by":"publisher","award":["PTDC\/QUI-QFI\/2870\/2020","CEECINST\/00069\/2021","2022.13031.BD","UIDB\/00081\/2020","UIDB\/05748\/2020","LA\/P\/0056\/2020"],"award-info":[{"award-number":["PTDC\/QUI-QFI\/2870\/2020","CEECINST\/00069\/2021","2022.13031.BD","UIDB\/00081\/2020","UIDB\/05748\/2020","LA\/P\/0056\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Associated Laboratory IMS","doi-asserted-by":"publisher","award":["PTDC\/QUI-QFI\/2870\/2020","CEECINST\/00069\/2021","2022.13031.BD","UIDB\/00081\/2020","UIDB\/05748\/2020","LA\/P\/0056\/2020"],"award-info":[{"award-number":["PTDC\/QUI-QFI\/2870\/2020","CEECINST\/00069\/2021","2022.13031.BD","UIDB\/00081\/2020","UIDB\/05748\/2020","LA\/P\/0056\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Marine Coelenterazine is one of the most well-known chemi-\/bioluminescent systems, and in which reaction the chemi-\/bioluminophore (Coelenteramide) is generated and chemiexcited to singlet excited states (leading to light emission). Recent studies have shown that the bromination of compounds associated with the marine Coelenterazine system can provide them with new properties, such as anticancer activity and enhanced emission. Given this, our objective is to characterize the photophysical properties of a previously reported brominated Coelenteramide analog, by employing a combined experimental and theoretical approach. To better analyze the potential halogen effect, we have also synthesized and characterized, for the first time, two new fluorinated and chlorinated Coelenteramide analogs. These compounds show similar emission spectra in aqueous solution, but with different fluorescence quantum yields, in a trend that can be correlated with the heavy-atom effect (F &gt; Cl &gt; Br). A blue shift in emission in other solvents is also verified with the F\u2013Cl\u2013Br trend. More relevantly, the fluorescence quantum yield of the brominated analog is particularly sensitive to changes in solvent, which indicates that this compound has potential use as a microenvironment fluorescence probe. Theoretical calculations indicate that the observed excited state transitions result from local excitations involving the pyrazine ring. The obtained information should be useful for the further exploration of halogenated Coelenteramides and their luminescent properties.<\/jats:p>","DOI":"10.3390\/molecules27248875","type":"journal-article","created":{"date-parts":[[2022,12,14]],"date-time":"2022-12-14T03:21:52Z","timestamp":1670988112000},"page":"8875","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Combined Experimental and Theoretical Investigation into the Photophysical Properties of Halogenated Coelenteramide Analogs"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8806-230X","authenticated-orcid":false,"given":"Ana Carolina P.","family":"Afonso","sequence":"first","affiliation":[{"name":"Chemistry Research Unit (CIQUP), Institute of Molecular Sciences (IMS), Department of Geosciences, Environment and Territorial Planning, Faculty of Sciences, University of Porto, R. Campo Alegre s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0138-4929","authenticated-orcid":false,"given":"Patricia","family":"Gonz\u00e1lez-Berdullas","sequence":"additional","affiliation":[{"name":"Chemistry Research Unit (CIQUP), Institute of Molecular Sciences (IMS), Department of Geosciences, Environment and Territorial Planning, Faculty of Sciences, University of Porto, R. Campo Alegre s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8478-3441","authenticated-orcid":false,"given":"Joaquim C. G.","family":"Esteves da Silva","sequence":"additional","affiliation":[{"name":"Chemistry Research Unit (CIQUP), Institute of Molecular Sciences (IMS), Department of Geosciences, Environment and Territorial Planning, Faculty of Sciences, University of Porto, R. Campo Alegre s\/n, 4169-007 Porto, Portugal"},{"name":"LACOMEPHI, GreenUPorto, Department of Geosciences, Environment and Territorial Planning, Faculty of Sciences, University of Porto, R. Campo Alegre s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5647-8455","authenticated-orcid":false,"given":"Lu\u00eds","family":"Pinto da Silva","sequence":"additional","affiliation":[{"name":"Chemistry Research Unit (CIQUP), Institute of Molecular Sciences (IMS), Department of Geosciences, Environment and Territorial Planning, Faculty of Sciences, University of Porto, R. Campo Alegre s\/n, 4169-007 Porto, Portugal"},{"name":"LACOMEPHI, GreenUPorto, Department of Geosciences, Environment and Territorial Planning, Faculty of Sciences, University of Porto, R. Campo Alegre s\/n, 4169-007 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2286","DOI":"10.1002\/cphc.201600270","article-title":"Chemiluminescence and bioluminescence as an excitation source in the photodynamic therapy of cancer: A critical review","volume":"17","year":"2016","journal-title":"Chem. Phys. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6927","DOI":"10.1021\/acs.chemrev.7b00649","article-title":"Chemi- and bioluminescence of cyclic peroxides","volume":"118","author":"Vacher","year":"2018","journal-title":"Chem. Rev."},{"key":"ref_3","first-page":"4","article-title":"The elusive relationship between strucutre and colour emission in beetle luciferases","volume":"5","author":"Lui","year":"2021","journal-title":"Nat. Rev. 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