{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,17]],"date-time":"2025-11-17T17:22:08Z","timestamp":1763400128160,"version":"build-2065373602"},"reference-count":44,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2023,3,29]],"date-time":"2023-03-29T00:00:00Z","timestamp":1680048000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","award":["UIDB\/00100\/2020","UIDB\/04565\/2020","SFRH\/BD\/129323\/2017","COVID\/BD\/152147\/2022"],"award-info":[{"award-number":["UIDB\/00100\/2020","UIDB\/04565\/2020","SFRH\/BD\/129323\/2017","COVID\/BD\/152147\/2022"]}]},{"name":"PhD Grant ref.","award":["UIDB\/00100\/2020","UIDB\/04565\/2020","SFRH\/BD\/129323\/2017","COVID\/BD\/152147\/2022"],"award-info":[{"award-number":["UIDB\/00100\/2020","UIDB\/04565\/2020","SFRH\/BD\/129323\/2017","COVID\/BD\/152147\/2022"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The binding behaviour of two ureido-hexahomotrioxacalix[3]arene derivatives bearing naphthyl (1) and pyrenyl (2) fluorogenic units at the lower rim towards selected nitroaromatic compounds (NACs) was evaluated. Their affinity, or lack of it, was determined by UV-Vis absorption, fluorescence and NMR spectroscopy. Different computational methods were also used to further investigate any possible complexation between the calixarenes and the NACs. All the results show no significant interaction between calixarenes 1 and 2 and the NACs in either dichloromethane or acetonitrile solutions. Moreover, the fluorescence quenching observed is only apparent and merely results from the absorption of the NACs at the excitation wavelength (inner filter effect). This evidence is in stark contrast with reports in the literature for similar calixarenes. A naphthyl urea dihomooxacalix[4]arene (3) is also subject to the inner filter effect and is shown to form a stable complex with trinitrophenol; however, the equilibrium association constant is greatly overestimated if no correction is applied (9400 M\u22121 vs 3000 M\u22121), again stressing the importance of taking into account the inner filter effect in these systems.<\/jats:p>","DOI":"10.3390\/molecules28073052","type":"journal-article","created":{"date-parts":[[2023,3,30]],"date-time":"2023-03-30T01:31:30Z","timestamp":1680139890000},"page":"3052","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Critical Analysis of Association Constants between Calixarenes and Nitroaromatic Compounds Obtained by Fluorescence. Implications for Explosives Sensing"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8727-7077","authenticated-orcid":false,"given":"Alexandre S.","family":"Miranda","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Faculdade de Ci\u00eancias, Universidade de Lisboa, Edif\u00edcio C8, 1749-016 Lisboa, Portugal"},{"name":"IBB-Institute for Bioengineering and Biosciences, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7297-5139","authenticated-orcid":false,"given":"Paula M.","family":"Marcos","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Faculdade de Ci\u00eancias, Universidade de Lisboa, Edif\u00edcio C8, 1749-016 Lisboa, Portugal"},{"name":"Faculdade de Farm\u00e1cia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5535-2500","authenticated-orcid":false,"given":"Jos\u00e9 R.","family":"Ascenso","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Instituto Superior T\u00e9cnico, Complexo I, Av. Rovisco Pais, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2946-1498","authenticated-orcid":false,"given":"M\u00e1rio N.","family":"Berberan-Santos","sequence":"additional","affiliation":[{"name":"IBB-Institute for Bioengineering and Biosciences, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6134-2093","authenticated-orcid":false,"given":"Peter J.","family":"Cragg","sequence":"additional","affiliation":[{"name":"School of Applied Sciences, Huxley Building, University of Brighton, Brighton BN2 4GJ, UK"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2433-8773","authenticated-orcid":false,"given":"Rachel","family":"Schurhammer","sequence":"additional","affiliation":[{"name":"Laboratoire de Mod\u00e9lisation et Simulations Mol\u00e9culaires, Universit\u00e9 de Strasbourg, UMR 7140, F-67000 Strasbourg, France"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2409-2849","authenticated-orcid":false,"given":"Christophe","family":"Gourlaouen","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie Quantique, Universit\u00e9 de Strasbourg, UMR 7177, F-67000 Strasbourg, France"}]}],"member":"1968","published-online":{"date-parts":[[2023,3,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"8019","DOI":"10.1039\/C5CS00496A","article-title":"Fluorescence based explosive detection: From mechanisms to sensory materials","volume":"44","author":"Sun","year":"2015","journal-title":"Chem. 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