ArticleNature protocols2016
Preparative scale and convenient synthesis of a water-soluble, deep cavitand.
Article in Nature protocols, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- A Column Chromatography-Free Protocol for the Synthesis of Water-Soluble Cavitands.The Journal of organic chemistry · 2025Article
- HFIP as a versatile solvent in resorcin[Beilstein journal of organic chemistry · 2024Article
- Smartphone-Based Dopamine Detection by Fluorescent Supramolecular Sensor.Molecules (Basel, Switzerland) · 2022Article
- Influence of water-soluble pillararene hosts on Kemp elimination.RSC advances · 2021Article
- Selective discrimination and classification of G-quadruplex structures with a host-guest sensing array.Nature chemistry · 2021Article
- Recognition of Hydrophilic Cyclic Compounds by a Water-Soluble Cavitand.Molecules (Basel, Switzerland) · 2021Article
- Sensing of citrulline modifications in histone peptides by deep cavitand hosts.Chemical communications (Cambridge, England) · 2019Article
- The aqueous supramolecular chemistry of cucurbit[n]urils, pillar[n]arenes and deep-cavity cavitands.Chemical Society reviews · 2017Review
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Authors and funding
3 authors.
Funding
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Abstract
Cavitands are established tools of supramolecular chemistry and molecular recognition, and they are finding increasing application in sensing and sequestration of physiologically relevant molecules in aqueous solution. The synthesis of a water-soluble, deep cavitand is described. The route comprises six (linear) steps from commercially available precursors, and it relies on the fourfold oligomeric cyclization reaction of resorcinol with 2,3-dihydrofuran that leads to the formation of a shallow resorcinarene framework; condensation with aromatic panels, which deepens the hydrophobic binding cavity; construction of rigid urea functionalities on the upper rim; and the introduction of the water-solubilizing methylimidazolium groups on the lower rim. Late intermediates of the synthesis can be used in the preparation of congener cavitands with different properties and applications, and a sample of such a synthetic procedure is included in this protocol. Emphasis is placed on scaled-up reactions and on purification procedures that afford materials in high yield and avoid chromatographic purification. This protocol provides improvements over previously described procedures, and it enables the preparation of sizable amounts of deep cavitands: 7 g of a water-soluble cavitand can be prepared from resorcinol in 13 working days.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.