{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,30]],"date-time":"2026-03-30T22:01:37Z","timestamp":1774908097662,"version":"3.50.1"},"reference-count":44,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2020,10,14]],"date-time":"2020-10-14T00:00:00Z","timestamp":1602633600000},"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":["UID\/QUI\/00100\/2013; UIDB\/00100\/2020"],"award-info":[{"award-number":["UID\/QUI\/00100\/2013; UIDB\/00100\/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>Fluorescent dihomooxacalix[4]arene-based receptors 5a\u20135c, bearing two naphthyl(thio)ureido groups at the lower rim via a butyl spacer, were synthesised and obtained in the cone conformation in solution. The X-ray crystal structures of 1,3- (5a) and 3,4-dinaphthylurea (5b) derivatives are reported. Their binding properties towards several anions of different geometries were assessed by 1H-NMR, UV-Vis absorption and fluorescence titrations. Structural and energetic insights of the naphthylurea 5a and 5b complexes were also obtained using quantum mechanical calculations. The data showed that all receptors follow the same trend, the association constants increase with the anion basicity, and the strongest complexes were obtained with F\u2212, followed by the oxoanions AcO\u2212 and BzO\u2212. Proximal urea 5b is a better anion receptor compared to distal urea 5a, and both are more efficient than thiourea 5c. Compounds 5a and 5b were also investigated as heteroditopic receptors for biologically relevant alkylammonium salts, such as the neurotransmitter \u03b3-aminobutyric acid (GABA\u00b7HCl) and the betaine deoxycarnitine\u00b7HCl. Chiral recognition towards the guest sec-butylamine\u00b7HCl was also tested, and a 5:2 selectivity for (R)-sec-BuNH3+\u00b7Cl\u2212 towards (P) or (M) enantiomers of the inherently chiral receptor 5a was shown. Based on DFT calculations, the complex [(S)-sec-BuNH3+\u00b7Cl\u2212\/(M)-5a] was indicated as the more stable.<\/jats:p>","DOI":"10.3390\/molecules25204708","type":"journal-article","created":{"date-parts":[[2020,10,17]],"date-time":"2020-10-17T08:14:50Z","timestamp":1602922490000},"page":"4708","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Dihomooxacalix[4]arene-Based Fluorescent Receptors for Anion and Organic Ion Pair Recognition"],"prefix":"10.3390","volume":"25","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, Faculdade de Ci\u00eancias da Universidade de Lisboa, Edif\u00edcio C8, 1749-016 Lisboa, Portugal"},{"name":"IBB\u2013Institute 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, Faculdade de Ci\u00eancias da 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\/0000-0002-2946-1498","authenticated-orcid":false,"given":"Jos\u00e9 R.","family":"Ascenso","sequence":"additional","affiliation":[{"name":"Instituto Superior T\u00e9cnico, CQE, 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\u2013Institute for Bioengineering and Biosciences, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal"}]},{"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\/0000-0003-1271-5719","authenticated-orcid":false,"given":"Neal","family":"Hickey","sequence":"additional","affiliation":[{"name":"Department of Chemical and Pharmaceutical Sciences, Centre of Excellence in Biocrystallography, University of Trieste, via L. Giorgieri 1, 34127 Trieste, Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0711-5113","authenticated-orcid":false,"given":"Silvano","family":"Geremia","sequence":"additional","affiliation":[{"name":"Department of Chemical and Pharmaceutical Sciences, Centre of Excellence in Biocrystallography, University of Trieste, via L. Giorgieri 1, 34127 Trieste, Italy"}]}],"member":"1968","published-online":{"date-parts":[[2020,10,14]]},"reference":[{"key":"ref_1","unstructured":"Gutsche, C.D. (2008). Calixarenes: An Introduction: Edition 2, The Royal Society of Chemistry. [2nd ed.]. Monographs in Supramolecular Chemistry."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Neri, P., Sessler, J.L., and Wang, M.-X. (2016). Calixarenes and Beyond, Springer International Publishing.","DOI":"10.1007\/978-3-319-31867-7"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Neri, P., Sessler, J.L., and Wang, M.-X. (2016). Fluorescent calixarene hosts. 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