Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
The complexation properties of two novel C5-substituted adamantanediazirines within the resorcin[4]arene-based cavitand 4 were investigated in DMSO-d(6), revealing that binding is up to 1.4 kcal/mol stronger for halogenated adamantanediazirines when compared with the unsubstituted species. The thermal behavior of 5-bromo-2-aziadamantane (3) was investigated by DSC analysis as the first representative of the adamantanediazirine family in the neat solid state, as well as encapsulated within the aromatic cavity of cavitand 4. In the solid phase, the reactions of photolytically or thermolytically generated 5-bromo-2-adamantanylidene (11) can be controlled by complexation within cavitand 4.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol902667a | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A Column Chromatography-Free Protocol for the Synthesis of Water-Soluble Cavitands.
J Org Chem
July 2025
Department of Science and Technological Innovation, University of Eastern Piedmont, Via Michel 11, Alessandria 15121, Italy.
An efficient synthetic protocol for the synthesis of a library of unprecedented resorcin[4]arene-based water-soluble molecular containers is reported here. Key to this approach is the tetra-iodo derivative , named "" (KIC), which acts as a concave-shaped scaffold for the synthesis of deep-cavitands via Sonogashira coupling. Most of the deep-cavitands described in this study are synthesized without chromatographic processes, leading to a faster purification, ready accessibility, and easier scale-up, while also offering a different cavity in terms of size and shape compared to the current ones.
View Article and Find Full Text PDFModeling Binding Selectivity of Xylene Isomers in Resorcin[4]arene-Based Organo- and Metallo-Cavitands.
J Org Chem
July 2025
Department of Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.
Binding of xylene isomers to two resorcin[4]arene-based water-soluble cavitands, one fully organic and one with palladium bridges, is investigated by means of a combination of molecular dynamics simulations and quantum chemical calculations. Experimentally, the metallo-cavitand binds all three isomers but shows a preference for -xylene, while the organo-cavitand prefers -xylene and shows no affinity for -xylene. The cavitands are first characterized and compared in aqueous solution in the absence of guests using classical molecular dynamics simulations.
View Article and Find Full Text PDFAnion-Directed Self-Assembly of Calix[4]arene-Based Silver(I) Coordination Polymers and Photocatalytic Degradation of Organic Pollutants.
Inorg Chem
February 2023
Key Laboratory of Green Preparation and Application for Functional Materials, Ministry of Education, Hubei Key Laboratory of Polymer Science, School of Materials Science and Engineering, Hubei University, Wuhan, Hubei 430062, P.R. China.
Coordination polymers (CPs) have recently emerged as promising candidates for heterogeneous photocatalysis due to their structural designability and tunable properties. Herein, we developed two novel Ag(I)-calix[4]arene coordination polymers with the formula {[Ag(μ-NO)]} (CP ) and {[Ag]·PF} (CP ) ( = 2-mercapto-5-methyl-1,3,4-thiadiazole resorcinol calix[4]arene). Crystallography revealed that anion coordination and self-inclusion behavior induced the cavitand and silver ions to self-assemble into well-defined CPs and with different topological coordination frameworks, respectively.
View Article and Find Full Text PDFMolecular Recognition with Resorcin[4]arene Cavitands: Switching, Halogen-Bonded Capsules, and Enantioselective Complexation.
J Am Chem Soc
February 2018
Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich , Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.
The development of synthetic host-guest chemistry to investigate and quantify weak, non-covalent interactions has been key to unraveling the complexity of molecular recognition in chemical and biological systems. Macrocycles have shown great utility in the design of receptors, enabling the development of highly preorganized structures. Among macrocycles, resorcin[4]arene-based cavitands have become privileged scaffolds due to their synthetic tunability, which allows access to structures with precisely defined geometries, as well as receptors that display conformational switching between two distinct states with a large difference in guest-binding properties.
View Article and Find Full Text PDFSystematic Investigation of Resorcin[4]arene-Based Cavitands as Affinity Materials on Quartz Crystal Microbalances.
Chempluschem
March 2017
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Resorcin[4]arene cavitands are well-known supramolecular hosts, and their outstanding guest-binding abilities in solution have been studied in detail in recent decades. In a systematic approach, different resorcin[4]arene cavitands and container molecules are characterized as affinity materials for gravimetric sensing using high-fundamental-frequency quartz crystal microbalances. Analysis of their affinity toward a series of various analytes reveals a remarkable dependence of both selectivity and sensitivity on the shape, accessibility, and size of the cavity, along with their supramolecular interactions with the host molecules.
View Article and Find Full Text PDF