Probing Weak Intermolecular Interactions in Self-Assembled Nanotubes

Bouteiller, Laurent; Schoot, Paul van der

doi:10.1021/ja210706v

Cited by 25 publications

(24 citation statements)

References 18 publications

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“…47 In toluene both structures have similar stabilities and are in fast dynamic exchange. [48][49] Therefore, it is possible to switch the assembly from one structure to the other by changing the temperature: the high-temperature structure is a long filament with a single bis-urea in the cross-section, 16 while the low-temperature structure is a very long and rigid tube with three bis-ureas in the cross-section ( Figure 1). 50,51 The latter structure is particularly interesting as the entanglements between the nanotubes are responsible for the formation of viscoelastic gels 22,[51][52][53][54] and the presence of a tubular cavity opens the door to ultramicroporous materials.…”

Section: Resultsmentioning

confidence: 99%

Conformational Control of Hydrogen-Bonded Aromatic Bis-Ureas

et al. 2012

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The phenylurea moiety is a ubiquitous synthon in supramolecular chemistry because it contains strong complementary hydrogen bonding groups and is synthetically very accessible. Here we investigate the possibility to strengthen self-association by conformational preorganization of the phenylurea moiety. In fact, we show that it is possible to strongly enhance intermolecular interactions between hydrogen bonded aromatic bis-ureas by substitution at the ortho positions of the phenylurea groups. Ortho substituents enforce a noncoplanar conformation of the urea and phenyl moieties better suited for hydrogen bonding. Substitution by methyl groups is more efficient than with larger groups, probably because of reduced steric hindrance. These effects have been demonstrated in the case of two different supramolecular architectures, which points to the probable generality of the phenomenon. In addition, this study has led to the discovery of a new bis-urea able to form very stable self-assembled nanotubes in toluene up to high temperatures (boiling point) or low concentrations (10(-7) M) and in chloroform down to 3 × 10(-4) M.

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Section: Resultsmentioning

confidence: 99%

Conformational Control of Hydrogen-Bonded Aromatic Bis-Ureas

et al. 2012

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“…A few years ago, we reported on a supramolecular balance concept that is well suited to quantify weak intermolecular effects in solution 33,34 because of its extreme sensitivity compared to similar approaches. 35,36 We now apply this concept to determine whether XX interactions can be detected and quantified in solution at room temperature.…”

Section: Introductionmentioning

confidence: 99%

Probing halogen–halogen interactions in solution

Ayzac

Raynal

Isare

et al. 2017

Phys. Chem. Chem. Phys.

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a Halogen-halogen interactions are a particularly interesting class of halogen bonds that are known to be essential design elements in crystal engineering. In solution, it is likely that halogen-halogen interactions also play a role, but the weakness of this interaction makes it difficult to characterize or even simply detect. We have designed a supramolecular balance that allows to detect Br … Br interactions between CBr3 groups in solution and close to room temperature. The sensitivity and versatility of the chosen platform has allowed to accumulate consistent data.In halogenoalkane solvents, we propose estimates for the free energy of these weak halogen bond interactions. In toluene solutions, we show that the interactions between Br atoms and the solvent aromatic groups dominate over the Br … Br interactions.

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“…When state A is thermodynamically more stable than state B, and so K e,A > K e,B , the maximum concentration of free monomers in the system is determined by the stability of polymer A and not polymer B (see eq 2). However, at temperatures close to the transition between the polymer states, the stabilities of the supramolecular polymers are very similar 22,24 and the monomers have a large tendency to be aggregated. Consequently, when polymer state B is only weakly cooperative and nucleation of state B occurs relatively easily, the small amount of free monomers can already assemble into supramolecular polymers of state B, even when state B is not the most stable thermodynamic structure.…”

Section: Introductionmentioning

confidence: 99%

Counterintuitive consequences of competitive pathways in supramolecular polymerizations

Mabesoone

Meijer

2019

Journal of Polymer Science

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Competition between supramolecular polymers for the same monomers can lead to strong responses in these systems. Using numerical simulations, we show that the sharpness and asymmetry of the transition from one thermodynamically stable polymer to another upon changing temperature is determined by the most unstable rather than the most stable supramolecular polymer. The width and asymmetry of the transitions are shown to depend on the relative and absolute nucleation penalties of the competing supramolecular polymerizations.

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Probing Weak Intermolecular Interactions in Self-Assembled Nanotubes

Cited by 25 publications

References 18 publications

Conformational Control of Hydrogen-Bonded Aromatic Bis-Ureas

Conformational Control of Hydrogen-Bonded Aromatic Bis-Ureas

Probing halogen–halogen interactions in solution

Counterintuitive consequences of competitive pathways in supramolecular polymerizations

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