Tricyclic octaurea “Temples” for the recognition of polar molecules in water

Webster, Claire S; Balduzzi, Federica; Davis, Anthony P.

doi:10.1039/d2ob02061k

Cited by 6 publications

(4 citation statements)

References 42 publications

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“…Tetra-carboxylate [1 bÀ 4H] 4À and tetra-ammonium [2 + 4H] 4 + derivatives were soluble in neutral water (pH ~7) at millimolar concentration and in a wide range of pHs (5)(6)(7)(8)(9)(10)(11). Both receptors formed thermodynamically stable 1 : 1 inclusion complexes with pyridine N-oxide 4 a and phenyl pyridine Noxide 4 b in water at pH 7 (Table 1 and Figure 4).…”

Section: Aryl-extended Calix[4]pyrroles Aeà C[4]psmentioning

confidence: 99%

“…For example, they synthesized a temple receptor featuring identical bis-urea spacer groups but changed the receptor's roof and bottom to a pyrene derivative. [8] In contrast to the strong carbohydrate-binding exhibited by the mesitylene derivative, the pyrene counterpart did not bind carbohydrates in water. The authors attributed the obtained results to the hydrophobic collapse of the binding cavity for the mesitylene derivative.…”

Section: Introductionmentioning

confidence: 96%

“…Based on the outstanding results obtained with this receptor, the Davis’ group recently explored the binding behavior of related molecular designs. For example, they synthesized a temple receptor featuring identical bis‐urea spacer groups but changed the receptor's roof and bottom to a pyrene derivative [8] . In contrast to the strong carbohydrate‐binding exhibited by the mesitylene derivative, the pyrene counterpart did not bind carbohydrates in water.…”

Section: Introductionmentioning

confidence: 99%

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Water‐Soluble Aryl‐ and Super Aryl‐Extended Calix[4]pyrroles

Aragay

Ballester

2023

Israel Journal of Chemistry

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The study of molecular recognition processes in water using biomimetic synthetic receptors provides valuable information for understanding more complex biological processes. In the last decade, our group focused on the use of aryl‐extended calix[4]pyrrole (AE−C[4]P) scaffolds for the binding of small polar molecules in water. The cone conformation of tetra‐α isomers of aryl‐extended calix[4]pyrroles defines a deep hydrophobic cavity with an open end and functionalized with converging hydrogen‐bond donor groups in its closed end. In this sense, AE−C[4]Ps can be considered as simple biomimetic analogs of enzyme binding sites. In this account, we describe the synthetic strategies used for the preparation of water‐soluble AE‐ and super aryl‐extended (SAE−) C[4]Ps. We review and rationalize the results of their molecular recognition studies in water using pyridyl‐N‐oxide derivatives and a series of small and neutral polar molecules as guests and comment on their applications as supramolecular and sequestering protective groups.

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Section: Aryl-extended Calix[4]pyrroles Aeà C[4]psmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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Water‐Soluble Aryl‐ and Super Aryl‐Extended Calix[4]pyrroles

Aragay

Ballester

2023

Israel Journal of Chemistry

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“…Their behavior as bidentate ligands bearing an electron-donor center (carbonyl oxygen) and two acidic protons confers them with singular properties to be used for several purposes. For instance, they are employed as organocatalysts to activate and induce asymmetry in several reactions due to their ability to coordinate simultaneously with an electrophile and a nucleophilic reagent, as well as for hydrogen bonding. − Another substantial use of ureas is in the field of molecular recognition, especially in host–guest interactions. − …”

Section: Introductionmentioning

confidence: 99%

Chiral Cyclobutane-Based Ureas as Versatile Platforms to Tune Structural Diversity: An Experimental and Theoretical Approach

Illa,

Da Silva,

Torres

et al. 2024

Crystal Growth & Design

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Four new chiral 2,2′-disubstituted biscyclobutane ureas have been synthesized and crystallized. Each of them bears a different substituent on positions 2,2′, that is, esters, hydroxymethyl groups, and carboxyl groups. The mode of aggregation of each urea in the crystal packing to form chains, helices, sheets, and others is tuned both by the intermolecular hydrogen bonds between the urea groups and by the different ability of the substituents to generate extra hydrogen bonding. Experimental results have been rationalized with the aid of computational calculations, which allow to understand the contribution of the energetic factors to the stabilization of the preferential structures observed.

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Low‐Symmetry Macrocycles and Cages for Carbohydrate Recognition

2023

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The recognition of carbohydrate plays a key role in numerous biological processes. Thus, artificial receptors have been synthesized to mimic these biological systems. To date, most of the receptors reported for carbohydrate complexation present highly symmetrical cavities, probably because their syntheses require less synthetic efforts and are easier to achieve and control. However, carbohydrates display complex, asymmetrical structures suggesting that hosts with low symmetry might be more adapted to recognize these guests. Here, we described the strategies that have been used to complex carbohydrates with macrocycles and cages presenting low symmetry and the potential of this approach. Self-assembled cages are first described, then covalent macrocycles and cages are presented and for each example the binding properties of low-symmetry systems are compared to those of their higher-symmetry counterparts.

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Tricyclic octaurea “Temples” for the recognition of polar molecules in water

Abstract: Two water-soluble tricyclic “Temple” macrocycles featuring pyrene roof/floor units and bis-urea spacers have been synthesised and studied as receptors for aromatic compounds in aqueous media. The tricycles show good selectivity...

Cited by 6 publications

References 42 publications

Water‐Soluble Aryl‐ and Super Aryl‐Extended Calix[4]pyrroles

Water‐Soluble Aryl‐ and Super Aryl‐Extended Calix[4]pyrroles

Chiral Cyclobutane-Based Ureas as Versatile Platforms to Tune Structural Diversity: An Experimental and Theoretical Approach

Low‐Symmetry Macrocycles and Cages for Carbohydrate Recognition

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