One‐step Access to Resorcinsalens—Solvent‐Dependent Synthesis, Tautomerism, Self‐sorting and Supramolecular Architectures of Chiral Polyimine Analogues of Resorcinarene

Szymkowiak, Joanna; Warżajtis, Beata; Rychłewska, Urszula; Kwit, Marcin

doi:10.1002/chem.201800316

Cited by 14 publications

(6 citation statements)

References 41 publications

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“…They can act as hosts for small organic guest molecules, form dimers and capsules or self-associate into larger structures. The formation of various noncovalent aggregates of these macrocycles was demonstrated by Kwit, Janiak and others for solid, liquid, and gas phases [88][89][90][91][92][93][94][95].…”

Section: [3 + 3] Macrocyclesmentioning

confidence: 88%

Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

Lisowski

2022

Molecules

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The condensation of aromatic dialdehydes with chiral diamines, such as 1,2-trans-diaminocyclohexane, leads to various enantiopure or meso-type macrocyclic Schiff bases, including [2 + 2], [3 + 3], [4 + 4], [6 + 6] and [8 + 8] condensation products. Unlike most cases of macrocycle synthesis, the [3 + 3] macrocycles of this type are sometimes obtained in high yields by direct condensation without a metal template. Macrocycles of other sizes from this family can often be selectively obtained in high yields by a suitable choice of metal template, solvent, or chirality of the building blocks. In particular, the application of a cadmium(II) template results in the expansion of the [2 + 2] macrocycles into giant [6 + 6] and [8 + 8] macrocycles. These imine macrocycles can be reduced to the corresponding macrocyclic amines which can act as hosts for the binding of multiple cations or multiple anions.

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Section: [3 + 3] Macrocyclesmentioning

confidence: 88%

Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

Lisowski

2022

Molecules

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“…Within 3 hours, the macrocycles start to tautomerise to the keto‐enamine forms, which is associated with precipitation of the hardly soluble solids. The same reactions conducted in boiling ethanol provided [2+2] macrocycles M5a′ ‐ M5c′ appeared as keto‐enamine tautomers at once …”

Section: Detailed Look At Polyimine Macrocyclesmentioning

confidence: 92%

“…The polyimine derivatives of isophthalaldehyde and its heteroaromatic congeners are named “isotrianglimines ”, whereas set of “ rhombimines ” consists of [2+2] macrocyclic derivatives of the dialdehydes characterized by the presence of two aryl units connected by the same single atom or by the aryl group (the OHC⋅⋅⋅CHO angle equals to 120°). A particular case represents the family of mono‐ and dihydroxyisophthalaldehydes providing vase‐like macrocycles dubbed “ calixsalens ” or “ resorcinsalens ” ,. Other salen‐containing polyimine macrocycles (not discussed here) have taken their name from the structurally closest class of unsubstituted macrocycles by adding the suffix “ salen ” (see Scheme ).…”

Section: Factors For the Favorable Synthesis Of Polyimine Macrocyclesmentioning

confidence: 99%

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One‐Step Construction of the Shape Persistent, Chiral But Symmetrical Polyimine Macrocycles

Kwit

Grajewski

Skowronek

et al. 2018

The Chemical Record

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A unique combination of structural flexibility, shape persistency and functionality, makes macrocycles and molecular cages as essential molecular entities that have displayed applications that go beyond chemistry. Among macrocycles, the selectively obtained symmetrical (poly)cyclic polyimines have shown great utility in the design of molecules varied in shape and properties. The reversible and thermodynamically controlled cycloimination reaction is governed by configurational and conformational constraints imposed on the intermediate products, ensures a sufficiently high level of preorganization. The high geometrical control over the macrocycle structure has profound effect on their assembly mode. In this Account, we were interested in showing how the structure of small building blocks affects the structure of macrocyclic product and further, how influenced the association mode of the given macromolecule. The latter is of primarily importance in supramolecular and in material chemistry.

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“…Similarly, the recognition and self-organization phenomena characteristic for complex biological systems have triggered research in many areas of chemistry. Both social self-sorting (self-discrimination) and narcissistic self-sorting (self-recognition) are examples of such phenomena that attract increasing attention. − …”

Section: Introductionmentioning

confidence: 99%

Sorting Phenomena and Chirality Transfer in Fluoride-Bridged Macrocyclic Rare Earth Complexes

et al. 2021

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The reaction of fluoride anions with mononuclear lanthanide(III) and yttrium(III) hexaaza-macrocyclic complexes results in the formation of dinuclear fluoride-bridged complexes. As indicated by X-ray crystal structures, in these complexes two metal ions bound by the macrocycles are linked by two or three bridging fluoride anions, depending on the type of the macrocycle. In the case of the chiral hexaaza-macrocycle L1 derived from trans -1,2-diaminocyclohexane, the formation of these μ 2 -fluorido dinuclear complexes is accompanied by enantiomeric self-recognition of macrocyclic units. In contrast, this kind of recognition is not observed in the case of complexes of the chiral macrocycle L2 derived from 1,2-diphenylethylenediamine. The reaction of fluoride with a mixture of mononuclear complexes of L1 and L2, containing two different Ln(III) ions, results in narcissistic sorting of macrocyclic units. Conversely, a similar reaction involving mononuclear complexes of L1 and complexes of achiral macrocycle L3 based on ethylenediamine results in sociable sorting of macrocyclic units and preferable formation of heterodinuclear complexes. In addition, formation of these heterodinuclear complexes is accompanied by chirality transfer from the chiral macrocycle L1 to the achiral macrocycle L3 as indicated by CPL and CD spectra.

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One‐step Access to Resorcinsalens—Solvent‐Dependent Synthesis, Tautomerism, Self‐sorting and Supramolecular Architectures of Chiral Polyimine Analogues of Resorcinarene

Cited by 14 publications

References 41 publications

Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

One‐Step Construction of the Shape Persistent, Chiral But Symmetrical Polyimine Macrocycles

Sorting Phenomena and Chirality Transfer in Fluoride-Bridged Macrocyclic Rare Earth Complexes

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