Preprint Article Version 1 This version is not peer-reviewed

Structural Conformations of Calixarene-Based Receptors and Their Implications for Molecular Recognition

Version 1 : Received: 1 August 2024 / Approved: 2 August 2024 / Online: 2 August 2024 (11:54:01 CEST)

How to cite: Saitz, C.; Ochoa, A.; Hernández-Arancibia, B.; Herrera- Muñoz, J.; Gómez- Machuca, H. Structural Conformations of Calixarene-Based Receptors and Their Implications for Molecular Recognition. Preprints 2024, 2024080174. https://doi.org/10.20944/preprints202408.0174.v1 Saitz, C.; Ochoa, A.; Hernández-Arancibia, B.; Herrera- Muñoz, J.; Gómez- Machuca, H. Structural Conformations of Calixarene-Based Receptors and Their Implications for Molecular Recognition. Preprints 2024, 2024080174. https://doi.org/10.20944/preprints202408.0174.v1

Abstract

We have synthesized and examined a series of calix[4]arene-based chemosensors containing thiosemicarbazone or thiourea as a binding site and a pyridine-chromophore unit in various conformations. These conformations include pinched cone (I), cone (III and IV), and 1,3-alternate (II and V). Our objective was to assess the binding abilities of these sensors towards anions and cations using different spectroscopic techniques. All receptors demonstrate the ability to recognize cations, with notable distinctions between them. Receptor I demonstrates a broad spectrum of ion recognition, encompassing Ag+, Cu2+, Co2+, Ni2+, and Zn2+. Receptors IV and V also exhibit complex formation with Co2+, Ni2+, and Cu2+ ions. Sensors II and III demonstrate exceptional selectivity for recognizing the copper (II) ion. When studying anions, only receptor I yielded satisfactory results. This is due to the thiosemicarbazone bridge and its spatial orientation in the pinched cone conformation, which allows for an interaction to occur. It is worth noting that sensors IV and V, which are fluorescent molecules due to the triazolo pyridine unit in their structure, exhibit particularly noteworthy behavior. The highest association constant is observed for cobalt (II) complexes, with values of 6.59 and 2.38 (x1012 mol/L)-2 for receptors IV and V, respectively. Our findings indicate that there are no significant differences in selectivity and sensitivity between ca-lix[4]arene receptors in 1,3-alternate and cone conformations.

Keywords

Calix[4]arene; Conformations; Receptor; Bifunctional.

Subject

Chemistry and Materials Science, Organic Chemistry

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