Dynamic Molecular Recognition in Solid State for Separating Mixtures of Isomeric Dicarboxylic Acids

Užarević, Krunoslav; Halász, Ivan; Đilović, Ivica; Bregović, Nikola; Rubčić, Mirta; Matković‐Čalogović, Dubravka; Tomišić, Vladislav

doi:10.1002/anie.201301032

Cited by 48 publications

(31 citation statements)

References 40 publications

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“…2 The second class of often studied receptors comprises those with the ability to change their conformation in order to respond to the specific demands of the anionic template (geometry, charge density, pH-dependent behaviour, etc.). [11][12][13] Two principal sets of the receptor conformations were observed in the obtained crystal structures, denoted as C-and Z-conformers (Scheme 1b). 6 In this context, the study of the interaction modes between the flexible receptor and flexible or multifaceted anions (such as linear thiocyanate or pyramidal chlorate) could prove especially interesting and lead to further developments in the field.…”

Section: Introductionmentioning

confidence: 99%

Conformational adaptations of acyclic receptor templated by weakly coordinating anions

Đilović

Užarević

2015

CrystEngComm

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Crystallization from methanol solutions resulted in new supramolecular complexes of a flexible polyamine receptor N,N′-3-azapentane-1,5-bisĳ3-Ĳ1-aminoethylidene)-6-methyl-3H-pyran-2,4-dione] (L) with spherical (Br − and I − ), linear (SCN − ) or pyramidal ĲClO 3 − ) anions. The recognition and self-assembly processes yielded five solids: solvated (1a) and non-solvated (1b) forms of HL : SCN − complex with quite different receptor conformations, a supramolecular complex with ClO 3 − anion (3), which is isoskeletal to 1b, and HL : Br − (2) and HL : I − complexes which are isoskeletal to 1a. It is shown that the rich coordinating potential of the anions investigated arises not only from their geometry but also from their ambivalent accepting functionalities. The divergence in the way binding occurs is reflected on supramolecular synthons stabilizing crystal structures as well as on the physicochemical properties of the obtained solids. In these systems, anion binding could be interpreted as a competition between two "solvation spheres", one provided by the solvent molecules and the other dominated by high-order supramolecular receptors built from HL molecules. This behaviour is related to previously reported complexes of HL with trigonal, tetrahedral and octahedral anions, emphasizing the receptor's conformational adaptability for providing the most favourable surrounding for guest inclusion in the rigid environment of a crystal. Scheme 1 (a) Protonated polyamine receptor HL. (b) In complexes with anions, HL adopts different conformers depending on the relative orientation of methyl groups -syn-C (orange), anti-C (red), syn-Z (green) and anti-Z (blue). The conformers assemble in high-order supramolecular receptors [as in (c) or (d)] or supramolecular polymers [in (e)]. Hydrogen atoms and anions were omitted for clarity.

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Section: Introductionmentioning

confidence: 99%

Conformational adaptations of acyclic receptor templated by weakly coordinating anions

Đilović

Užarević

2015

CrystEngComm

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“…[8][9][10][11][12] Also, Schiff bases have been intensively used as synthetic intermediates 13 and, more recently, as anion receptors. [14][15][16] They have attracted particular interest due to their biological activity 17,18 and as model systems for biological macromolecules. 19,20 Solid-state thermochromism and photochromism are another characteristic of these compounds leading to their application in various areas of materials science.…”

Section: Introductionmentioning

confidence: 99%

Controlling Solvate Formation of a Schiff Base by Combining Mechano-chemistry with Solution Synthesis

et al. 2012

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Abstract. A Schiff base dicarboxylic acid (1) was prepared by condensation of 2-hydroxy-1-naphthaldehyde with 5-aminoisophthalic acid. Its solvates with pyridine (2a and 2b) and dimethylformamide (3) were prepared by liquid-assisted grinding and by conventional solvent-based methods. All products were characterised by FT-IR spectroscopy, thermogravimetric analysis and differential scanning calorimetry. The structures of 1, 2b and 3 were determined by single crystal X-ray diffraction. 1 was found to be a pure Schiff base, 2b a pyridine solvate and 3 a dimethylformamide solvate monohydrate. In all three structures, the Schiff base molecule appears to be present as the ketoamine tautomer.(doi: 10.5562/cca2111)

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“…[4] At the other end of the volume scale there are organic salts of T N,N'-3-azoniapentane-1,5-diylbis(3-(1-aminoethylidene)-6-methyl-2H-pyran-2,4(3H)-dione) that have an extremely large unit cell volume (72951 Å 3 , Figure 2, CSD refcode YOHFUX). [5] This huge unit cell contains 96 individual formula units (Z = 96) but only half of the formula unit is symmetry unique (Z' = 0.5).…”

Section: Croatian Chemical Crystallographymentioning

confidence: 99%

“…One of the largest Croatian structures in the CSD by unit cell volume, an organic salt in space group Fd-3c (CSD refcode YOHFUX). [5] Figure 3. Chart of the number of crystal structures contributed by Dr Kojić-Prodić to the CSD over the years with breakdown into organic (green line), metal-organic (blue line) and polymeric systems (purple line).…”

Section: Biserka and The Csdmentioning

confidence: 99%

A Historical Perspective on Crystallography in Croatia and the Career of Biserka Kojić-Prodić from the Viewpoint of the CSD

et al. 2018

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There is a long history of chemical crystallography and use of the Cambridge Structural Database (CSD) in Croatia, which dates back to 1985 when the CSD first became accessible there thanks to the efforts of Biserka Kojić-Prodić as head of the National Affiliated Centre. On the occasion of Dr Kojić-Prodić's 80 th birthday we take the opportunity to look back at the history of crystallography in Croatia, and particularly in Biserka's career, from the point of view of the CSD. Biserka has been a prolific author and contributor of crystal structures over the years sharing over 400 structures and collaborating with over 270 different co-authors on a wide range of different types of structure.

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Dynamic Molecular Recognition in Solid State for Separating Mixtures of Isomeric Dicarboxylic Acids

Cited by 48 publications

References 40 publications

Conformational adaptations of acyclic receptor templated by weakly coordinating anions

Conformational adaptations of acyclic receptor templated by weakly coordinating anions

Controlling Solvate Formation of a Schiff Base by Combining Mechano-chemistry with Solution Synthesis

A Historical Perspective on Crystallography in Croatia and the Career of Biserka Kojić-Prodić from the Viewpoint of the CSD

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