{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,28]],"date-time":"2025-11-28T22:26:25Z","timestamp":1764368785693,"version":"build-2065373602"},"reference-count":37,"publisher":"MDPI AG","issue":"16","license":[{"start":{"date-parts":[[2021,8,22]],"date-time":"2021-08-22T00:00:00Z","timestamp":1629590400000},"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 a Tecnologia","doi-asserted-by":"publisher","award":["UIDB\/50006\/2020","PTDC\/QUI-QIN\/28142\/2017","PTDC\/QUI-QOR\/29426\/2017","DFA\/BD\/9136\/2020"],"award-info":[{"award-number":["UIDB\/50006\/2020","PTDC\/QUI-QIN\/28142\/2017","PTDC\/QUI-QOR\/29426\/2017","DFA\/BD\/9136\/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>Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs). Several amines including n- and t-butylamine, cadaverine, and putrescine cause spectral changes of 4, in UV\u2013Vis and fluorescence spectra, which are indicative of their potential application as an effective tool to detect amines in acetonitrile solutions. In the gas phase, the probe response is more expressive for spermine and putrescine. Additionally, we found that methanolic solutions of rosamine 4 and n-butylamine undergo a pink to yellow color change over time, which has been attributed to the formation of a new compound. The latter was isolated and identified as 5 (9\u2212aminopyronin), whose solutions exhibit a remarkable increase in fluorescence intensity together with a shift toward more energetic wavelengths. Other 9-aminopyronins 6a, 6b, 7a, and 7b were obtained from methanolic solutions of 4 with putrescine and cadaverine, demonstrating the potential of this new xanthene entity to react with primary amines.<\/jats:p>","DOI":"10.3390\/molecules26165082","type":"journal-article","created":{"date-parts":[[2021,8,22]],"date-time":"2021-08-22T21:47:52Z","timestamp":1629668872000},"page":"5082","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1923-2218","authenticated-orcid":false,"given":"Filipe","family":"Monteiro-Silva","sequence":"first","affiliation":[{"name":"Centre for Applied Photonics, INESC TEC, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0485-8023","authenticated-orcid":false,"given":"Carla","family":"Queir\u00f3s","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 4169-007 Porto, Portugal"}]},{"given":"Andreia","family":"Leite","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 4169-007 Porto, Portugal"}]},{"given":"Mar\u00eda T.","family":"Rodr\u00edguez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Burgos, 09001 Burgos, Spain"}]},{"given":"Mar\u00eda J.","family":"Rojo","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Burgos, 09001 Burgos, Spain"}]},{"given":"Tom\u00e1s","family":"Torroba","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Burgos, 09001 Burgos, Spain"}]},{"given":"Rui C.","family":"Martins","sequence":"additional","affiliation":[{"name":"Centre for Applied Photonics, INESC TEC, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0393-1655","authenticated-orcid":false,"given":"Ana M. G.","family":"Silva","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua do Campo Alegre, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0998-1437","authenticated-orcid":false,"given":"Maria","family":"Rangel","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Instituto de Ci\u00eancias Biom\u00e9dicas de Abel Salazar, Rua Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2021,8,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"8271","DOI":"10.1039\/C4CS00185K","article-title":"Jack of all trades: Versatile catechol crosslinking mechanisms","volume":"43","author":"Yang","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Kim, J., Lee, C., and Ryu, J.H. (2020). 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