Self‐Assembly of Ureido‐Pyrimidinone Dimers into One‐Dimensional Stacks by Lateral Hydrogen Bonding

Nieuwenhuizen, Marko M. L.; Greef, Tom F. A. de; Bruggen, Rob L. J. van der; Paulusse, Jos M. J.; Appel, Wilco P. J.; Smulders, Maarten M. J.; Sijbesma, Rint P.; Meijer, E. W.

doi:10.1002/chem.200902107

Cited by 95 publications

(36 citation statements)

References 74 publications

(37 reference statements)

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“…However, in a report on the self-assembly of ureido-pyrimidinones, which exhibit intermolecular lateral hydrogen bonds between the urea group, the mechanism of supramolecular polymerization has been reported to follow an isodesmic process. [52] But the cooling curves obtained seem to be non-sigmoidal and almost linear. Thus, we expect that monitoring of other properties that change upon polymerization (such as viscosity) as a function of temperature might give a better representation of the mechanism involved.…”

Section: Discussionmentioning

confidence: 94%

What Molecular Features Govern the Mechanism of Supramolecular Polymerization?

2012

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An understanding of the mechanisms of supramolecular polymerization from a molecular point of view is lacking. Several reports in the literature on the mechanism exhibited by different classes of molecules are examined in an attempt to correlate the molecular features to the aggregation pathway followed. It is proposed that long-range interactions between oligomers could lead to their cooperative growth. The lack thereof leads to isodesmicity.

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Section: Discussionmentioning

confidence: 94%

What Molecular Features Govern the Mechanism of Supramolecular Polymerization?

2012

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“…Once the monomer-dimer model was discarded, the isodesmic model was proposed for the aggregation of the compounds under study. [28] In this model, which has been successfully applied to describe the p-p stacking of several molecules such as perylene bisimides, [27][28][29][30] hexabenzocoronenes [31] or phenylene ethynylene macrocycles, [32] the same association constant, K, value is assumed for all the binding processes. [33] In applying the isodesmic model, we calculated the association constants of all the compounds and subsequently confirmed the applicability of the model.…”

Section: Aggregation Model and Association Constantsmentioning

confidence: 99%

NMR Spectroscopic Study of the Self‐Aggregation of 3‐Hexen‐1,5‐diyne Derivatives

Pérez

Saá

Ballesteros

et al. 2013

Chemistry A European J

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The self‐assembly of polycatenar molecules derived from 1,6‐diphenyl‐3,4‐dipropyl‐3‐hexen‐1,5‐diyne has been studied in detail by solution NMR spectroscopy. The analysis of the concentration‐ and temperature‐dependent evolution of the chemical shifts and the diffusion coefficients in [D12]cyclohexane agrees well with an isodesmic model of association in this solvent. The association constants for the stacking and entropy and enthalpy of the process have been obtained. The driving force for the aggregation process is provided by a negative enthalpy (ΔH), which is partially compensated by a negative entropy (ΔS). A structural study of the self‐assembly in solution has been carried out with the help of NOESY NMR spectroscopic experiments.

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“…10.18) [45]. Regarding the urea-substituted molecule, the formation of the 1-D stacks was due to the lateral aggregation of urea-hydrogen bonding and their additional stabilization by the aromatic-aromatic π-π stacking confirmed by the concentration-dependent 1 H NMR and DOSY spectroscopy.…”

Section: Supramolecular Polymers Constructed By Orthogonalmentioning

confidence: 80%

Hydrogen-Bonded Supramolecular Polymers

Chen

Xiao

2015

Lecture Notes in Chemistry

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Supramolecular polymers constructed by different kinds of low-molecularweight monomers or high-molecular-weight conventional polymeric species based on hydrogen bonding interactions have attracted more and more attention due to their fascinating and unconventional chemical and physical properties. A series of multiple hydrogen-bonding building blocks are described herein, which make the expansion of the research field of hydrogen-bonded supramolecular polymers and allow the fabrication of more new and functional supramolecular polymers. This chapter focuses on linear hydrogen-bonded supramolecular polymers and networks which are described in three parts. The first part is the main-chain supramolecular polymers, in which the polymeric backbone is constructed by noncovalently bonded lowmolecular-weight monomers. The second part is the conventional polymer-based supramolecular polymers, in which the main polymeric backbone part is constructed by covalently bonded conventional polymer, but functionalized by hydrogen-bonding motifs. The last part is supramolecular polymers constructed by orthogonal hydrogen bonding-driven self-assembly and other noncovalent interactions. IntroductionIn view of the reversible and dynamic nature of noncovalent interactions, supramolecular polymers have attracted much attention in recent years as they not only possess conventional polymeric properties, but also show new distinct material properties, which ensure their potential application in a broad range of fields [1][2][3][4][5]. The secondary interactions involved in the construction of the supramolecular structures include hydrogen bonding, metal-ligand coordination, π-π stacking, ionic interaction, and host-guest interaction etc. Each of these noncovalent interactions

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Self‐Assembly of Ureido‐Pyrimidinone Dimers into One‐Dimensional Stacks by Lateral Hydrogen Bonding

Cited by 95 publications

References 74 publications

What Molecular Features Govern the Mechanism of Supramolecular Polymerization?

What Molecular Features Govern the Mechanism of Supramolecular Polymerization?

NMR Spectroscopic Study of the Self‐Aggregation of 3‐Hexen‐1,5‐diyne Derivatives

Hydrogen-Bonded Supramolecular Polymers

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