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Search Results (4)

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Keywords = water soluble resorcinarene

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11 pages, 3137 KB  
Article
Molecular Interaction of Water-Soluble Resorcinarenes for Potential Choline Detectors
by Cielo Urquijo, Miguel Vela, Roger Sarmiento and Mauricio Maldonado
Processes 2025, 13(2), 553; https://doi.org/10.3390/pr13020553 - 16 Feb 2025
Cited by 1 | Viewed by 1145
Abstract
The molecular interactions of water-soluble crown resorcinarenes with choline were analyzed. To this end, four sulfonated resorcinarenes were synthesized and characterized by ATR-IR, 1H-NMR, and 13C-NMR spectroscopy. The molecular interaction studies with choline were carried out through FT-IR spectroscopy, 1H-NMR [...] Read more.
The molecular interactions of water-soluble crown resorcinarenes with choline were analyzed. To this end, four sulfonated resorcinarenes were synthesized and characterized by ATR-IR, 1H-NMR, and 13C-NMR spectroscopy. The molecular interaction studies with choline were carried out through FT-IR spectroscopy, 1H-NMR titrations, and conductimetric titrations, with which it was possible to determine that the complexes formed 1:1 stoichiometries with the host, in addition to showing good interaction in the electronic cavity of the macrocycle, demonstrating great potential for host–guest systems for choline detection in aqueous media. Finally, the incidence of the structural aspects of sulfonated resorcinarenes were analyzed. Full article
(This article belongs to the Section Pharmaceutical Processes)
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23 pages, 7207 KB  
Article
Water-Soluble Polyglycidol-Grafted Ladder Calix Resorcinarene Oligomers with Open Chain and Cyclic Topologies: Synthesis, Characteristics, and Biological Evaluation
by Hristo Penchev, Erik Dimitrov, Christo Novakov, Emi Haladjova, Ralitsa Veleva, Veselina Moskova-Doumanova, Tanya Topouzova-Hristova and Stanislav Rangelov
Polymers 2024, 16(22), 3219; https://doi.org/10.3390/polym16223219 - 20 Nov 2024
Viewed by 1548
Abstract
Ladder oligomers containing calixarene skeletons in the main chain—calix[4]resorcinarene (CRA) ladder macromolecules with open chain and cyclic macromolecules with double ring-like (Noria-type) topologies—bring particular research attention as functional materials with various applications. However, there is still a remarkable lack of studies into the [...] Read more.
Ladder oligomers containing calixarene skeletons in the main chain—calix[4]resorcinarene (CRA) ladder macromolecules with open chain and cyclic macromolecules with double ring-like (Noria-type) topologies—bring particular research attention as functional materials with various applications. However, there is still a remarkable lack of studies into the synthesis of fully water-soluble derivatives of these interesting macromolecules. Research on this topic would allow their bio-based research and application niche to be at least revealed. In the present study, a strategy for the synthesis of water-soluble polyglycidol-derivatized calix resorcinarene ladder oligomers with open chain and cyclic structures is introduced. A grafting from approach was used to build branched or linear polyglycidol chains from the ladder scaffolds. The novel structures were synthesized in quantitative yields and fully characterized by NMR, FTIR and UV–vis spectroscopy, gel permeation chromatography, MALDI-TOF mass spectrometry, analytical ultracentrifugation, and static light scattering to obtain the molar mass characteristics and composition. The biocompatibility and toxicity of the two polyglycidol-derivatized oligomers were investigated and the concentration dependence of the survival of three cell lines of human origin determined. The selective apoptosis effect at relatively low dissolve concentrations toward two kinds of cancerous cell lines was found. Full article
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8 pages, 1611 KB  
Article
Water Soluble Host–Guest Chemistry Involving Aromatic N-Oxides and Sulfonateresorcinarene
by Kwaku Twum, Nicholas Schileru, Bianca Elias, Jordan Feder, Leena Yaqoo, Rakesh Puttreddy, Małgorzata M. Szczesniak and Ngong Kodiah Beyeh
Symmetry 2020, 12(11), 1751; https://doi.org/10.3390/sym12111751 - 22 Oct 2020
Cited by 5 | Viewed by 2721
Abstract
Resorcinarenes decorated with sulfonate groups are anionic in nature and water soluble with a hydrophobic electron-rich interior cavity. These receptors are shown to bind zwitterionic aromatic mono-N-oxides and cationic di-N-oxide salts with varying spacer lengths. Titration data fit a [...] Read more.
Resorcinarenes decorated with sulfonate groups are anionic in nature and water soluble with a hydrophobic electron-rich interior cavity. These receptors are shown to bind zwitterionic aromatic mono-N-oxides and cationic di-N-oxide salts with varying spacer lengths. Titration data fit a 1:1 binding isotherm for the mono-N-oxides and 2:1 binding isotherm for the di-N-oxides. The first binding constants for the di-N-oxides (K1: 104 M−1) are higher compared to the neutral mono-N-oxide (K: 103 M−1) due to enhanced electrostatic attraction from a receptor with an electron-rich internal cavity and cationic and electron deficient N-oxides. The interaction parameter α reveals positive cooperativity for the di-N-oxide with a four-carbon spacer and negative cooperativity for the di-N-oxides that have spacers with more four carbons. This is attributed to shape complementarity between the host and the guest. Full article
(This article belongs to the Special Issue Recent Advances in Structural and Synthetic Supramolecular Systems)
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14 pages, 1465 KB  
Article
Synthesis and Characterization of Two Sulfonated Resorcinarenes: A New Example of a Linear Array of Sodium Centers and Macrocycles
by Edilma Sanabria, Miguel Ángel Esteso, Adrián Pérez-Redondo, Edgar Vargas and Mauricio Maldonado
Molecules 2015, 20(6), 9915-9928; https://doi.org/10.3390/molecules20069915 - 28 May 2015
Cited by 34 | Viewed by 7469
Abstract
Two sulfonated resorcinarenes were synthesized by reacting C-tetra(butyl) resorcinarene or C-tetra(2-(methylthio)ethyl)resorcinarene with formaldehyde in the presence of sodium sulfite. Their structures were determined via FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. Thermal gravimetric analyses of the derivatives were also carried [...] Read more.
Two sulfonated resorcinarenes were synthesized by reacting C-tetra(butyl) resorcinarene or C-tetra(2-(methylthio)ethyl)resorcinarene with formaldehyde in the presence of sodium sulfite. Their structures were determined via FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. Thermal gravimetric analyses of the derivatives were also carried out and revealed the presence of water molecules in the solid state. The sulfonated product of C-tetra(butyl)resorcinarene was characterized by an X-ray crystal structure determination. The asymmetric unit contains eight molecules of water and two of acetone, and analysis indicated that sulfonated resorcinarene prefers a cone configuration (rccc conformation) in the solid state. In the crystal array, classical hydrogen bond interactions O-H···O and intermolecular contacts were observed. In the crystal packing, a linear array of capsules of sulfonated resorcinarenes was generated for a chain of sodium atoms and sulfonate groups. Full article
(This article belongs to the Section Organic Chemistry)
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