A Tautoleptic Approach to Chiral Hydrogen‐Bonded Supramolecular Tubular Polymers with Large Cavity

Neniškis, Algirdas; Račkauskaitė, Dovilė; Shi, Qixun; Robertson, Aiden J.; Marsh, Andrew; Ulčinas, Artūras; Valiokas, Ramūnas; Brown, Steven P.; Wärnmark, Kenneth; Orentas, Edvinas

doi:10.1002/chem.201803701

Cited by 9 publications

(5 citation statements)

References 47 publications

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“…The enantiopure bicyclo[3.3.1]nonane scaffold appended with two H-bonding units at each end was selected as the working unit based on the previous successful utilization of similar compounds in creating extremely stable square-shaped or tubular cavity aggregates. − The nearly 90° angle between the complementary ends renders these monomers highly preorganized for tetrameric cyclic aggregation. Moreover, their chirality-assisted aggregation provides full control over the formation of cavity aggregates and excludes the competing formation of unwanted zig-zag type H-bonded polymers.…”

Section: Results and Discussionmentioning

confidence: 99%

Fully Supramolecular Chiral Hydrogen-Bonded Molecular Tweezer

et al. 2022

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Molecular tweezers are open-ended, cavity-possessing U-shaped molecular architectures with high potential for various applications in supramolecular chemistry. Their covalent synthesis, however, is often tedious and the structures obtained lack structural responsiveness beyond the limited conformational flexibility of the scaffold. Herein we present a proof-of-concept study on the design, synthesis, assembly, and transformations of a novel supramolecular constructa fully noncovalent molecular tweezer. The supramolecular tweezer was assembled from a set of four building blocks, composed of two identical molecular angle bars and two flat aromatic extension wings, using hydrogen bonding only. The chirality-assisted aggregation process was utilized to ensure scaffold bending directionality using enantiomerically pure bicyclic angle bars. To address the challenges associated with shifting of the equilibrium from strong cooperative narcissistic self-sorting of self-complementary angle bars in cyclic aggregates toward integrative self-sorting in molecular tweezers, a rational desymmetrization strategy was applied. The dynamic supramolecular tweezer has been shown to display rich supramolecular chemistry, allowing for stimuli-responsive change in aggregate topology and solvent-responsive supramolecular polymerization.

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Section: Results and Discussionmentioning

confidence: 99%

Fully Supramolecular Chiral Hydrogen-Bonded Molecular Tweezer

et al. 2022

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“…7). 48 In that case, three DDA-AAD H-bonds between two different tautomeric isocytosine units led to the agregation into cyclic tetramers that stacked on top of each other resulting in chiral tubular ensembles (Fig. 7b and d).…”

Section: Nanotubementioning

confidence: 99%

Chiral nanotubes self-assembled from discrete non-covalent macrocycles

Chamorro

Aparicio

2021

Chem. Commun.

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“…11b). More recently, the authors published the study of related systems that can further aggregate into tubular supramolecular polymers by establishing orthogonal H-bonding interactions, 114,116 and in which the addition of C70 guests may induce such polymerization transition. 114 A recent study by Chamorro et al also disclosed evidence for synergic relationships between H-bonded macrocycles and carbon nanomaterials, in this case (6,5)SWCNTs (Single-Walled Carbon Nanotubes).…”

Section: Template Effectsmentioning

confidence: 99%