A homochiral tripodal receptor with selectivity for sodium (R)-2-aminopropionate over sodium (S)-2-aminopropionate

“…Howarth et al reported a homochiral tripodal imidazolium system (3) which could distinguish between sodium (R)-2aminopropionate and sodium (S)-2-aminopropionate. 7 From the 1 H NMR experiments, it is reported that the imidazolium salt forms a complex with the (R) enantiomer but not with the (S) enantiomer.…”

Section: Benzene Tripodal Systemsmentioning

confidence: 99%

Imidazolium receptors for the recognition of anions

et al. 2006

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“…In one study, using rigid skeleton trypticene derivatives, we showed, for the first time, an OSDA stabilization of VFI, an 18-ring sieve with a crosssection pore of 12 Å. 11 Subsequently, borrowing on a facile one-step synthesis from the organic chemistry literature, 12 used a triquaternary OSDA where three equal groups (built from 1,2 dimethyl imidazole) are tethered to an aromatic center through benzylic linkages. The OSDA is shown in Figure 1 and the folding into the guest lattice LTA is shown in Figure 2.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Germanosilicate Molecular Sieves from Mono- and Di-Quaternary Ammonium OSDAs Constructed from Benzyl Imidazolium Derivatives: Stabilization of Large Micropore Volumes Including New Molecular Sieve CIT-13

et al. 2016

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A series of monoquaternary and diquarternary benzyl-imidazolium derivatives are prepared and used as organic structure direction agents (OSDAs) in germanosilicate syntheses. The goal of this work is to create new multidimensional large pore zeolites. For the OSDA made and tested, we looked for relationships based upon stereochemistry from the benzyl ring as part of each structure. Several known molecular sieves with the *BEA, BEC, IWS, or LTA topologies are obtained. Molecular modeling is carried out with the goal of understanding: (a) the product selectivity correlation with the OSDA and the zeolite obtained, and (b) why differential rates of crystallization are observed for isomers that lead to different zeolite products. Additionally, a new molecular sieve denoted CIT-13 is prepared and shown to possess intersecting 14-and 10-membered ring pores, which gives confidence to the soundness of this approach for OSDA construction to yield new multidimensional large pore zeolites. CIT-13 is the first molecular sieve to have this combination of pore sizes.

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“…In contrast, the identically substituted triethylbenzene derivatives with three cationic recognition sites are unable to effectively complex Neu5Ac in aqueous media but showed strong binding in less competitive solvents, such as acetonitrile, as expected. At this point, it should be mentioned that studies with triethylbenzene-based compounds possessing three cationic groups, such as pyridinium, bipyridinium, quinolinium or imidazolium groups, have made a very important contribution to the field of anion recognition [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Motifs in the Crystal Structures of Triethylbenzene Derivatives Bearing Pyridinium Subunits in Combination with Pyrimidinyl or Pyridinyl Groups

Weiße,

Seichter,

Mazik

2023

Molecules

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A series of mono- and dicationic 1,3,5-trisubstituted 2,4,6-triethylbenzenes containing pyridinium groups in combination with aminopyrimidine-/aminopyridine-based recognition units were synthesized and crystallographically studied. The combination of neutral and ionic building blocks represents a promising strategy for the development of effective and selective artificial receptors for anionic substrates. In the crystalline state, the investigated compounds show a tendency to bind the counterion PF6− in the cavity formed by the three functionalized side-arms. The intermolecular interactions with the PF6− ion comprise N-H∙∙∙F and C-H∙∙∙F bonds. Detailed analysis of various supramolecular motifs, including interactions with solvent molecules, provides deeper insights into the processes of molecular recognition. The information obtained is useful in the development of new receptor molecules for anions and in the selection of the most appropriate counterion.

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A homochiral tripodal receptor with selectivity for sodium (R)-2-aminopropionate over sodium (S)-2-aminopropionate

Cited by 24 publications

References 19 publications

Imidazolium receptors for the recognition of anions

Imidazolium receptors for the recognition of anions

Synthesis of Germanosilicate Molecular Sieves from Mono- and Di-Quaternary Ammonium OSDAs Constructed from Benzyl Imidazolium Derivatives: Stabilization of Large Micropore Volumes Including New Molecular Sieve CIT-13

Supramolecular Motifs in the Crystal Structures of Triethylbenzene Derivatives Bearing Pyridinium Subunits in Combination with Pyrimidinyl or Pyridinyl Groups

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