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Squaramide-Based Receptors in Anion Supramolecular Chemistry: Insights Into Anion Binding, Sensing, Transport and Extraction [PDF]

Chemical Society Reviews
: Over the last 15 years, squaramide-based receptors have attracted the attention of supramolecular chemists working in the field of anion recognition. Herein, we highlight examples of squaramide-based receptors that are able to bind, sense, extract and ...
Riccardo Montis, Vito Lippolis, Giacomo Picci   +2 more
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Squaramides as Potent Transmembrane Anion Transporters

Angewandte Chemie International Edition, 2012
Square peg in a round ball: squaramides are shown to be potent transmembrane anion transporters for both chloride and bicarbonate, performing better than the thiourea and urea analogues. Studies into the nature of this transport point to a mobile carrier mechanism, where the squaramide delivers the anion cargo across the lipid bilayer (see scheme ...
Busschaert, Nathalie, Kirby, Isabelle L., Young, Sarah, Coles, Simon J., Horton, Peter N., Light, Mark E., Gale, Philip A.   +6 more
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Asymmetric Iodolactonization Utilizing Chiral Squaramides

Organic Letters, 2012
Asymmetric iodolactonization of γ- and δ-unsaturated carboxylic acids has been explored in the presence of six different chiral organocatalysts 5-8. The catalyst 6b was found to facilitate the cyclization of 5-arylhex-5-enoic acids 1 to the corresponding iodolactones 2 with up to 96% ee.
Jørn E, Tungen, Jens M J, Nolsøe, Trond V, Hansen   +2 more
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Squaramides: physical properties, synthesis and applications

Chemical Society Reviews, 2011
Squaramides are remarkable four-membered ring systems derived from squaric acid that are able to form up to four hydrogen bonds. A high affinity for hydrogen bonding is driven through a concomitant increase in aromaticity of the ring. This hydrogen bonding and aromatic switching, in combination with structural rigidity, have been exploited in many of ...
R Ian, Storer, Caroline, Aciro, Lyn H, Jones   +2 more
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Cooperativity in Solid-State Squaramides

Crystal Growth & Design, 2011
Using a dipyridyl squaramide derivative as a model, we have shown that cooperativity in hydrogen-bonded catemers plays a crucial role in defining the solid-state synthon of disecondary squaramides, overriding the preferred association mode in solution.
R. Prohens, A. Portell, C. Puigjaner, S. Tomas, K. Fujii, K. D. M. Harris, X. Alcobe, M. Font-Bardia, R. Barbas   +8 more
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π-Stacking Driven Aggregation and Folding of Squaramides

The Journal of Physical Chemistry A, 2020
Competing noncovalent interactions play a pivotal role in the folding and assembly of three-dimensional structures, especially in flexible molecules. Calculations using density functional theory reveal that two squaramide rings aggregate to form a slipped antiparallel π-stacked dimer with high propensity. This π-π stacking interaction is used to design
Saumik Sen, Arkaprabha Basu, Tirthendu Sen, G. Naresh Patwari   +3 more
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Squaramide-based Receptors for Anion Recognition

, 2017
A series of squaramide based receptors bearing benzene and pyridine linkers was developed, ranging from simple alkyl-substituted mono-squaramides to macrocyclic tri-squaramides by altering the number of squaramide binding sites, adjusting the geometries of compounds and appending different solubilizing groups.
Qin, Lei
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Copper-Mediated Synthesis of Tertiary Diaryl Squaramides

The Journal of Organic Chemistry, 2007
Tertiary aryl squaramides were synthesized by using copper catalyzed C-N bond-formation with L-proline as the ligand. Symmetrical diaryl squaramides could be prepared in a one-pot reaction by using excess aryl bromide with varying yields. Unsymmetrical derivatives were prepared by sequential arylation.
Vijayakumar, Ramalingam, Niala, Bhagirath, Rajeev S, Muthyala   +2 more
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Squaramide Formation for DNA-Encoded Library Synthesis

Bioconjugate Chemistry
DNA-encoded libraries (DELs) can be considered as one of the most powerful tools for the discovery of small molecules of biological interest. However, the ability to access large DELs is contingent upon having chemical transformations that work in aqueous phase and generate minimal DNA alterations and the availability of building blocks compatible with
Antoine Douchez, Julien Poupart, Gaoqiang Yang, Louis Vaillancourt, Anne Marinier   +4 more
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THE SQUARAMIDES. A NEW FAMILY OF HOST MOLECULES FOR CRYSTAL ENGINEERING

Molecular Crystals and Liquid Crystals, 2002
A host guest co-crystallization strategy for crystal engineering has been developed and a library of host molecules has been established. Each molecule possesses a hydrogen bond functionality that leads to the formation of a one-dimensional f -network with a characteristic repeat distance.
Yajun Liu, Alton H. W. Lam, Frank W. Fowler, Joseph W. Lauher   +3 more
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