Multiple Hydrogen-Bonded Complexes Based on 2-Ureido-4[1<i>H</i>]-pyrimidinone: A Theoretical Study

Sun, Hao; Lee, Hui Hui; Blakey, Idriss; Dargaville, Bronwin; Chirilă, Traian V.; Whittaker, Andrew K.; Smith, Sean C.

doi:10.1021/jp2061305

Cited by 29 publications

(32 citation statements)

References 59 publications

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“…It is noted that the water contact angle on polymer PBA–UPy7.2 decreased by about 10 degrees after a few minutes due to the overturning or migration of polar UPy groups at the polymer surface. Recent theoretical analysis shows that UPy–UPy binding energy can be reduced from ≈–161 kJ mol −1 in vacuum to –69 kJ mol −1 in water and that the binding energy of interaction between UPy and water molecules is competitive with that of UPy‐UPy . Temperature also has a significant impact on the self‐adhesion of PBA–UPy polymers.…”

Section: Resultsmentioning

confidence: 99%

“…For the PBA–UPy7.2 polymer, its higher T g , longer effective bond lifetime

τ_{normalb}^{*}

(≈3 vs ≈20 s), lower mobility of its chains and a stronger interaction due to the increased mole fraction of UPy groups make the PBA–UPy7.2 polymer more elastic than the PBA–UPy4.0 polymer and the diffusion of water molecules in the PBA–UPy7.2 film would be relatively more difficult than that for the PBA–UPy4.0 case . Increasing the relative humidity also dramatically increases the density of free UPy functional groups on the surface, and this effect is relatively more significant for PBA–Upy7.2 than for PBA–UPy4.0. The overall effect of relative humidity on the bulk viscoelastic properties (e.g., G′, G″) and surface chemistry ( γ values) of the two PBA–UPy polymers, is to increase their adhesion by ≈50% when increasing the relative humidity from 0% to 100% at room temperature.…”

Section: Resultsmentioning

confidence: 99%

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Adhesion and Surface Interactions of a Self‐Healing Polymer with Multiple Hydrogen‐Bonding Groups

Faghihnejad

Feldman

et al. 2014

Adv Funct Materials

217

156

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The surface properties and self‐adhesion mechanism of self‐healing poly(butyl acrylate) (PBA) copolymers containing comonomers with 2‐ureido‐4[1H]‐pyrimidinone quadruple hydrogen bonding groups (UPy) are investigated using a surface forces apparatus (SFA) coupled with a top‐view optical microscope. The surface energies of PBA–UPy4.0 and PBA–UPy7.2 (with mole percentages of UPy 4.0% and 7.2%, respectively) are estimated to be 45–56 mJ m−2 under dry condition by contact angle measurements using a three probe liquid method and also by contact and adhesion mechanics tests, as compared to the reported literature value of 31–34 mJ m−2 for PBA, an increase that is attributed to the strong UPy–UPy H‐bonding interactions. The adhesion strengths of PBA–UPy polymers depend on the UPy content, contact time, temperature and humidity level. Fractured PBA–UPy films can fully recover their self‐adhesion strength to 40, 81, and 100% in 10 s, 3 h, and 50 h, respectively, under almost zero external load. The fracture patterns (i.e., viscous fingers and highly “self‐organized” parallel stripe patterns) have implications for fabricating patterned surfaces in materials science and nanotechnology. These results provide new insights into the fundamental understanding of adhesive mechanisms of multiple hydrogen‐bonding polymers and development of novel self‐healing and stimuli‐responsive materials.

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Section: Resultsmentioning

confidence: 99%

“…For the PBA–UPy7.2 polymer, its higher T g , longer effective bond lifetime

τ_{normalb}^{*}

Section: Resultsmentioning

confidence: 99%

Adhesion and Surface Interactions of a Self‐Healing Polymer with Multiple Hydrogen‐Bonding Groups

Faghihnejad

Feldman

et al. 2014

Adv Funct Materials

217

156

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“…They investigated the influence of the contact time, temperature and humidity. Although theoretical analysis pointed out that the UPy–UPy binding energy decreases with increasing water content, a higher humidity unexpectedly led to stronger adhesion. Contact angle measurements demonstrated that surface migration of UPy groups was responsible for this.…”

Section: Adhesives Based On Hydrogen Bondingmentioning

confidence: 97%

Bioinspired Underwater Adhesives by Using the Supramolecular Toolbox

et al. 2018

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several excellent reviews. [9][10][11][12] Recently, it was emphasized by Waite that catechol moieties alone are insufficient to ensure proper underwater adhesion and that the performance is a complex interplay between DOPA and its local environment. [13] Therefore, attention is shifted to include other (noncovalent) interactions used in these natural glues, and much progress has been made in understanding both their performance and delivery process. [14] In this review, we take the sandcastle worm and mussel as a basis for inspiration. We discuss (noncovalent) interactions found in these natural adhesive systems and extend our discussion to additional supramolecular moieties that can be used to control the adhesive and cohesive performance of synthetically designed adhesives. In Section 2, we examine the natural systems and identify the versatile supramolecular interactions used in such protein-based adhesives. These include electrostatic interactions, hydrogen bonding, hydrophobic forces, π-π interactions, metal coordination, cation-π complexation, and dynamic covalent linkages. The use of these interactions in synthetic adhesive systems is explored in the subsequent sections. Section 3 is devoted to the different interactions that catechols (the functional group of DOPA) display to bond to a submerged substrate or to provide cohesive properties to the adhesive. Despite the fact that catechols have already been the topic of many excellent reviews, [9,13,17] we believe that catechols play a pivotal role in both the sandcastle worm and the mussel adhesive systems and, therefore, should not be omitted from this review. In Section 4, we discuss the use of electrostatic interactions in protein-based and synthetic adhesive formulations for wet conditions. These interactions can be tailored to a wide distribution of bond strengths and thus can be tuned to change multi ple mechanical properties, which is essential for design of an adhesive. Besides the effect on the adhesive and cohesive properties, we highlight work where electrostatic interactions cause liquid-liquid phase separation in aqueous polymer solutions. The resulting (complex) coacervate is a concentrated, liquid, yet water-insoluble phase of the adhesive material, which can act as a powerful delivery tool for underwater adhesives. Hydrogen bonding in adhesives is explored in Section 5. The use of hydrogen bonding to adjust the viscoelastic properties of adhesives has been identified decades, ago, and hydrogen bonding moieties are commonly used in pressure sensitive adhesives (PSAs). However, besides simple, single hydrogen bonding motifs, many interesting alternative Nature has developed protein-based adhesives whose underwater performance has attracted much research attention over the last few decades. The adhesive proteins are rich in catechols combined with amphiphilic and ionic features. This combination of features constitutes a supramolecular toolbox, to provide stimuli-responsive processing of the adhesive, to secure strong adhesion to a variety of...

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“…Density functional theory studies of UPy binding indicate that dimerization should not occur in water, although dimerization readily occurs in chloroform. 20 However, UPy association has been observed in water-swollen systems involving microphase segregated environments. For example, the non-polar microenvironments within UPy-containing block copolymer pluronics and aliphatic dendritic dimers promote UPy dimerization.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, swelling behavior, and viscoelastic properties of functional poly(hydroxyethyl methacrylate) with ureidopyrimidinone side-groups

Lewis

Anthamatten

2013

Soft Matter

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In this report the swelling and linear viscoelastic behavior of a hydrophilic polymer containing reversibly associating hydrogen bonding side-groups will be examined. Ureidopyrimidinone (UPy) moieties selfassociate to form hydrogen-bonded dimers (DDAA) in non-polar media; however, UPy behavior in water-swollen hydrogel environments is unclear. A series of technologically important, poly(hydroxyethyl methacrylate) (poly(HEMA)) polymers, with varying UPy side-group content, were prepared using a reversible addition-fragmentation chain transfer (RAFT) polymerization. Water swelling experiments revealed that UPy side-groups retard early time (<24 h) Fickian-like swelling and lead to two-stage, temperature-dependent, water sorption. At longer times UPy side-groups promote water swelling. Rheological studies show that the material's viscosity and viscous relaxation time both increase with increasing UPy-content. The activation energy of the shear-induced flow scales linearly with UPy-content, suggesting cooperative dynamics. These results are similar to observations made for hydrophobic polymers bearing hydrogen-bonding side-groups and suggest some UPy hydrogenbonding occurs in hydrated poly(HEMA), despite competitive H-bonding with water. Experimental observations can be explained by reversible association of UPy side-groups within water-excluded domains of poly(HEMA)'s secondary structure.

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Multiple Hydrogen-Bonded Complexes Based on 2-Ureido-4[1H]-pyrimidinone: A Theoretical Study

Cited by 29 publications

References 59 publications

Adhesion and Surface Interactions of a Self‐Healing Polymer with Multiple Hydrogen‐Bonding Groups

Adhesion and Surface Interactions of a Self‐Healing Polymer with Multiple Hydrogen‐Bonding Groups

Bioinspired Underwater Adhesives by Using the Supramolecular Toolbox

Synthesis, swelling behavior, and viscoelastic properties of functional poly(hydroxyethyl methacrylate) with ureidopyrimidinone side-groups

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