Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in <i>cone</i> and 1,3-<i>alternate</i> Conformations: Receptors for the Recognition of Ions
In this research we have synthesized and evaluated five calix[4]arene-based receptors functionalized with thiosemicarbazone or thiourea groups, incorporating pyridinyl naphthalene or triazolopyridine chromophores in 1,3-<i>alternate</i>, pinched <i>cone</i> and <i>cone&...
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MDPI AG
2025-02-01
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| author | Andrés Ochoa Belén Hernández-Arancibia José Herrera-Muñoz Horacio Gómez-Machuca Claudio Saitz |
| author_facet | Andrés Ochoa Belén Hernández-Arancibia José Herrera-Muñoz Horacio Gómez-Machuca Claudio Saitz |
| author_sort | Andrés Ochoa |
| collection | DOAJ |
| description | In this research we have synthesized and evaluated five calix[4]arene-based receptors functionalized with thiosemicarbazone or thiourea groups, incorporating pyridinyl naphthalene or triazolopyridine chromophores in 1,3-<i>alternate</i>, pinched <i>cone</i> and <i>cone</i> conformations. The ion recognition capabilities of these receptors were investigated using UV-visible and fluorescence spectroscopy. Receptor (<b>I</b>), which adopts a pinched <i>cone</i> conformation with thiosemicarbazone groups, demonstrated bifunctional sensing abilities by detecting both cations and anions. Receptors (<b>II</b>) and (<b>III</b>) showed remarkable selectivity and sensitivity for Cu<sup>2+</sup> ions. Receptors (<b>IV</b>) and (<b>V</b>), in <i>cone</i> and 1,3-<i>alternate</i> conformations, respectively, where functionalized with a triazolo[1,5-a]pyridine fluorophore and exhibited highly sensitive ON-OFF fluorescence sensing for Co<sup>2+</sup>, Cu<sup>2+</sup> and Ni<sup>2+</sup> ions, with significant fluorescence quenching upon binding and a low detection limit of 2.94 µg/L for the Co<sup>2+</sup> ion in receptor (<b>IV</b>). Ion receptor (<b>I</b>) demonstrates a strong performance in broad-spectrum ion detection, whereas the structural conformations of receptors (IV) and (V) play a pivotal role in their remarkable selectivity and sensitivity for specific transition metals in fluorescence-based sensing. |
| format | Article |
| id | doaj-art-4a6526e33adb47cfb68e983b97d6f3eb |
| institution | DOAJ |
| issn | 2227-9040 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
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| series | Chemosensors |
| spelling | doaj-art-4a6526e33adb47cfb68e983b97d6f3eb2025-08-20T02:44:52ZengMDPI AGChemosensors2227-90402025-02-011324810.3390/chemosensors13020048Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in <i>cone</i> and 1,3-<i>alternate</i> Conformations: Receptors for the Recognition of IonsAndrés Ochoa0Belén Hernández-Arancibia1José Herrera-Muñoz2Horacio Gómez-Machuca3Claudio Saitz4Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos 1007, Independencia, Santiago 8380492, ChileFacultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos 1007, Independencia, Santiago 8380492, ChileInstituto Universitario de Investigación y Desarrollo Tecnológico (IDT), Universidad Tecnológica Metropolitana, Ignacio Valdivieso 2409, San Joaquín, Santiago 8940577, ChileFacultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos 1007, Independencia, Santiago 8380492, ChileFacultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos 1007, Independencia, Santiago 8380492, ChileIn this research we have synthesized and evaluated five calix[4]arene-based receptors functionalized with thiosemicarbazone or thiourea groups, incorporating pyridinyl naphthalene or triazolopyridine chromophores in 1,3-<i>alternate</i>, pinched <i>cone</i> and <i>cone</i> conformations. The ion recognition capabilities of these receptors were investigated using UV-visible and fluorescence spectroscopy. Receptor (<b>I</b>), which adopts a pinched <i>cone</i> conformation with thiosemicarbazone groups, demonstrated bifunctional sensing abilities by detecting both cations and anions. Receptors (<b>II</b>) and (<b>III</b>) showed remarkable selectivity and sensitivity for Cu<sup>2+</sup> ions. Receptors (<b>IV</b>) and (<b>V</b>), in <i>cone</i> and 1,3-<i>alternate</i> conformations, respectively, where functionalized with a triazolo[1,5-a]pyridine fluorophore and exhibited highly sensitive ON-OFF fluorescence sensing for Co<sup>2+</sup>, Cu<sup>2+</sup> and Ni<sup>2+</sup> ions, with significant fluorescence quenching upon binding and a low detection limit of 2.94 µg/L for the Co<sup>2+</sup> ion in receptor (<b>IV</b>). Ion receptor (<b>I</b>) demonstrates a strong performance in broad-spectrum ion detection, whereas the structural conformations of receptors (IV) and (V) play a pivotal role in their remarkable selectivity and sensitivity for specific transition metals in fluorescence-based sensing.https://www.mdpi.com/2227-9040/13/2/48calix[4]areneconformationsreceptorbifunctional |
| spellingShingle | Andrés Ochoa Belén Hernández-Arancibia José Herrera-Muñoz Horacio Gómez-Machuca Claudio Saitz Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in <i>cone</i> and 1,3-<i>alternate</i> Conformations: Receptors for the Recognition of Ions Chemosensors calix[4]arene conformations receptor bifunctional |
| title | Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in <i>cone</i> and 1,3-<i>alternate</i> Conformations: Receptors for the Recognition of Ions |
| title_full | Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in <i>cone</i> and 1,3-<i>alternate</i> Conformations: Receptors for the Recognition of Ions |
| title_fullStr | Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in <i>cone</i> and 1,3-<i>alternate</i> Conformations: Receptors for the Recognition of Ions |
| title_full_unstemmed | Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in <i>cone</i> and 1,3-<i>alternate</i> Conformations: Receptors for the Recognition of Ions |
| title_short | Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in <i>cone</i> and 1,3-<i>alternate</i> Conformations: Receptors for the Recognition of Ions |
| title_sort | thiosemicarbazone and thiourea functionalized calix 4 arenes in i cone i and 1 3 i alternate i conformations receptors for the recognition of ions |
| topic | calix[4]arene conformations receptor bifunctional |
| url | https://www.mdpi.com/2227-9040/13/2/48 |
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