Controlling Surface Energy and Wetability with Diels−Alder Chemistry

Dirlam, Philip T.; Strange, Gregory A.; Orlicki, Joshua A.; Wetzel, Eric D.; Costanzo, Philip J.

doi:10.1021/la9032805

Cited by 29 publications

(31 citation statements)

References 24 publications

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“…More recently reversible Diels-Alder chemistry has been used to manipulate surface wettability of the silanized glass surfaces. 163 The relationship between the rate of an interfacial Diels-Alder reaction and the steric congestion around the reacting molecules has been studied in detail. 164 It was found that for monolayers presenting quinone groups (the dienophile) in an accessible environment, i.e.…”

Section: Diels-alder Reactionsmentioning

confidence: 99%

The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies

2011

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The modification of surfaces with self-assembled monolayers (SAMs) containing multiple different molecules, or containing molecules with multiple different functional components, or both, has become increasingly popular over the last two decades. This explosion of interest is primarily related to the ability to control the modification of interfaces with something approaching molecular level control and to the ability to characterise the molecular constructs by which the surface is modified. Over this time the level of sophistication of molecular constructs, and the level of knowledge related to how to fabricate molecular constructs on surfaces have advanced enormously. This critical review aims to guide researchers interested in modifying surfaces with a high degree of control to the use of organic layers. Highlighted are some of the issues to consider when working with SAMs, as well as some of the lessons learnt (169 references). 2011 The Royal Society of Chemistry. The modification of surfaces with self-assembled monolayers (SAMs) containing multiple different molecules, or containing molecules with multiple different functional components, or both, has become increasingly popular over the last two decades. This explosion of interest is primarily related to the ability to control the modification of interfaces with something approaching molecular level control and to the ability to characterise the molecular constructs by which the surface is modified. Over this time the level of sophistication of molecular constructs, and the level of knowledge related to how to fabricate molecular constructs on surfaces have advanced enormously. This critical review aims to guide researchers interested in modifying surfaces with a high degree of control to the use of organic layers. Highlighted are some of the issues to consider when working with SAMs, as well as some of the lessons learnt (169 references).

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Section: Diels-alder Reactionsmentioning

confidence: 99%

The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies

2011

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“…Other applications in the field of material science motivated the use of interfacial DA reactions from diene‐ or dienophile‐terminated silane assemblies. For instance, fluorinated compounds could be selectively immobilized by a DA reaction to control the wettability of the glass substrates . Fullerenes were grafted onto silicon wafers through DA reaction between C 60 and anthracene‐terminated monolayers to engineer transistors or sensors.…”

Section: Design Of Surfaces Able To React Via Interfacial Diels–aldermentioning

confidence: 99%

“…For instance, fluorinated compounds could be selectively immobilized by a DA reaction to control the wettability of the glass substrates. [114] Fullerenes were grafted onto silicon wafers through DA reaction between C 60 and anthracene-terminated monolayers [115] to engineer transistors or sensors. For applications in the field of nanocomposites, silica nanoparticles (often used as crosslinkers) were functionalized with maleimide groups and their reactivity with furan investigated.…”

Section: Interfacial Diels-alder Reaction On Monolayers or Silane Assmentioning

confidence: 99%

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Interfacial Thermoreversible Chemistry on Functional Coatings: A Focus on the Diels–Alder Reaction

Vauthier

Jierry

Oliveira

et al. 2018

Adv Funct Materials

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Stimuli‐responsive materials have properties that depend on the environment in which they are used. In most cases, the material itself is formulated to react to the corresponding stimulus. However, many phenomena occur at the surface of the material. In this context, the design and the investigation of the reactivity of stimuli‐responsive surfaces are particularly interesting. More precisely, this review focuses on functional coatings that react via Diels–Alder (DA) chemistry, a thermoreversible reaction between a diene and a dienophile. According to the nature of the substrate, these coatings are mainly based on self‐assembled monolayers or silane assemblies, on polydopamine derivatives, or on polymer thin films deposited by vapor‐phase processes including plasma polymerization. The different works discussed here show that interfacial thermoreversible reactions occur between a DA‐functionalized surface and a DA reactant in solution but also between two solid substrates are possible. The direct cycloaddition is always described in the cited papers but the reversibility of the reaction is less discussed. The latter however remains very challenging for smart applications in material science.

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“…Deux approches ontétéélaborées : la première repose sur le greffage de polymères parfaitement définis intégrant en extrémité de chaîne un motif catéchol et la seconde approche consisteà fonctionnaliser préalablement la surfaceà l'aide d'une ancre spécifique comportant d'une part le motif catéchol et d'autre part une entité susceptible de réagir avec une entité complémentaire dans le cadre d'une réaction réversible de cycloaddition de type Diels Alder [6].…”

Section: Introductionunclassified

Elaboration de plateformes biomimétiques à base de dopamine pour la fonctionnalisation du titane

Laure

Zobrist

Lyskawa

et al. 2013

MATEC Web of Conferences

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Abstract. The aim of this study concerns the functionalization of titanium surfaces by using versatile dopamine based on biomimetic anchors. This general concept was exploited to design new biomaterials which might be used as medical implants. In this context, two different grafting strategies based onto the "grafting to" approach were developed. The first one consisted on the synthesis and the immobilization of well-defined catechol end-functionalized polymers onto titanium surfaces. The second strategy was based on the functionalization of titanium surfaces by using dopamine derivates containing, on the one hand, a catechol unit for surface attachment and, on the other hand, a furan or a maleimide moiety able to react, on demand, through reversible Diels Alder (DA) reaction.Résumé. L'étude concerne la fonctionnalisation de surfacesà base de titaneà partir d'une ancre chimique biomimétique modifiable chimiquement, la dopamine, dans le but de concevoir des biomatériaux utilisables en tant que dispositifs implantables.Deux approches différentes de greffage par la stratégie «graft to» sont proposées. La première consiste en la synthèse et l'immobilisation sur les surfaces de titane de polymères parfaitement définis et stimulables fonctionnalisés par un motif catéchol en extrémité de chaîne. La seconde propose de modifier préalablement la surface par une ancre chimique spécifique intégrant un motif catéchol d'une part et un motif furane ou maléimide d'autre part permettant d'engager sur demande une réaction réversible de cycloaddition de type Diels Alder (DA) avec une large gamme de molécules ou polymères fonctionnalisés par l'entité complémentaire.

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Controlling Surface Energy and Wetability with Diels−Alder Chemistry

Cited by 29 publications

References 24 publications

The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies

The molecular level modification of surfaces: from self-assembled monolayers to complex molecular assemblies

Interfacial Thermoreversible Chemistry on Functional Coatings: A Focus on the Diels–Alder Reaction

Elaboration de plateformes biomimétiques à base de dopamine pour la fonctionnalisation du titane

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