Hydrophobic Collapse of Foldamer Capsules Drives Picomolar-Level Chloride Binding in Aqueous Acetonitrile Solutions

Hua, Yilei; Liu, Yun; Chen, Chun-Hsing; Flood, Amar H.

doi:10.1021/ja4074744

Cited by 178 publications

(142 citation statements)

References 98 publications

Supporting

Mentioning

135

Contrasting

Order By: Relevance

“…The combination of C−H hydrogen bonding and the hydrophobic effect has also been elegantly used by Flood and co‐workers for the recognition of chloride anions by the aryl‐triazole foldamer 18 in organic–aqueous solution (Figure 6 a) 104. Hydrophobic interactions are responsible for organizing and stabilizing the foldamer, which forms a 2:1 stoichiometric complex with chloride in 1:1 CH 3 CN/H 2 O solution, with about 80 % of the hydrophobic π surfaces buried within the duplex in the process.…”

Section: Small‐molecule Supramolecular Anion Receptorsmentioning

confidence: 99%

Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective

2015

View full text Add to dashboard Cite

The recognition of anions in water remains a key challenge in modern supramolecular chemistry, and is essential if proposed applications in biological, medical, and environmental arenas that typically require aqueous conditions are to be achieved. However, synthetic anion receptors that operate in water have, in general, been the exception rather than the norm to date. Nevertheless, a significant step change towards routinely conducting anion recognition in water has been achieved in the past few years, and this Review highlights these approaches, with particular focus on controlling and using the hydrophobic effect, as well as more exotic interactions such as C−H hydrogen bonding and halogen bonding. We also look beyond the field of small‐molecule recognition into the macromolecular domain, covering recent advances in anion recognition based on biomolecules, polymers, and nanoparticles.

show abstract

Section: Small‐molecule Supramolecular Anion Receptorsmentioning

confidence: 99%

Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective

2015

View full text Add to dashboard Cite

show abstract

“…Foldamers are one potential solution, and progress has been made in a few instances towards protein-like functionality. 47,48 Regarding host design, three points that the workshop frequently returned to are detailed below.…”

Section: [Insert Figure 2]mentioning

confidence: 99%

Collaborative routes to clarifying the murky waters of aqueous supramolecular chemistry

et al. 2017

Self Cite

View full text Add to dashboard Cite

Collaborative routes to clarifying the murky waters of aqueous supramolecular chemistry. AbstractOn planet Earth, water is everywhere: the majority of the surface is covered with it; it is a key component of all life; its vapor and droplets fill the lower atmosphere; even rocks contain it and undergo geomorphological changes because of it. A community of physical scientists largely drives studies of the chemistry of water and aqueous solutions, with expertise in biochemistry, spectroscopy, and computer modeling. More recently however, supramolecular chemistry -with its expertise in macrocyclic synthesis and measuring supramolecular interactions -have renewed their interest in water-mediated non-covalent interactions. These two groups offer complementary expertise that, if harnessed, offers to accelerate our understanding of aqueous supramolecular chemistry and water writ large. This review summarizes the state-of-the-art of the two fields, and highlights where there is latent chemical space for collaborative exploration by the two groups. 4Water is ubiquitous and essential to life on planet Earth. A full understanding of aqueous solutions is therefore of significance to a wide range of fields within the atmospheric, environmental, biological and geological sciences. Within the chemical sciences, a deeper appreciation of how non-covalent interactions and chemical transformations are influenced by water would benefit a variety of fields. However, as we highlight here, there are many open questions regarding the chemical and physical properties of aqueous solutions.The aqueous realm is frequently bifurcated into the Hofmeister and hydrophobic effects, phenomena that respectively deal with the properties of solutions of salts and relatively nonpolar molecules. However, it is becoming increasingly evident that these areas do in fact frequently overlap; two prime examples being the accumulation of large polarizable anions at the air-water interface, 1-5 and the favorable interactions of polarizable anions with non-polar surfaces. [6][7][8][9][10][11][12][13][14][15] Thus the hydrophobic and Hofmeister effects are but part of a greater continuum of aqueous supramolecular chemistry, with many important and outstanding questions regarding the influence of the different kinds of non-covalent interactions involved.Studies of water and aqueous solutions have mostly been driven by the physical sciences community, a broad range of scientists whose expertise in spectroscopy, computer modeling, and biochemistry (to name just three areas) has generally not involved macrocycles or host molecules in general. However, for some time now, supramolecular chemists -with their expertise in macrocyclic synthesis and measuring weak non-covalent interactions -have been travelling a parallel course of exploration. This Review, inspired by discussions between sixteen members of each community at a recent workshop, 16 is an attempt to summarize what we know about aqueous solutions, what we do not know about them, and where the two communit...

show abstract

“…Although examples of binding apolar guests in water on the basis of hydrophobic interactions are well known, Hua et al 23 demonstrated in a seminal report that hydrophobic interactions can be exploited to drive the binding of hydrophilic anions in aqueous solutions. The two aryl-triazole foldamers 49 and 50 ( Figure 16) were studied, in which the main chain could associate intramolecularly or intermolecularly via p-stacking, and the azobenzene unit further shielded the anion-binding site from solvents.…”

Section: Ch Hydrogen-bond-based Receptorsmentioning

confidence: 99%

Anion Receptor Chemistry

Gale

Howe

2016

Chem

376

228

View full text Add to dashboard Cite

Hydrophobic Collapse of Foldamer Capsules Drives Picomolar-Level Chloride Binding in Aqueous Acetonitrile Solutions

Cited by 178 publications

References 98 publications

Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective

Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective

Collaborative routes to clarifying the murky waters of aqueous supramolecular chemistry

Anion Receptor Chemistry

Contact Info

Product

Resources

About