A Retro-Diels−Alder Reaction to Uncover Maleimide-Modified Surfaces on Monolayer-Protected Nanoparticles for Reversible Covalent Assembly

Zhu, Jun; Kell, and Arnold J.; Workentin, Mark S.

doi:10.1021/ol0615937

Cited by 47 publications

(57 citation statements)

References 25 publications

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“…Thermally rDA reactions have been used in numerous studies including polymer synthesis [10][11][12][13][14][15][16][17], dendrimers [18][19][20][21], epoxy resins [22][23][24][25], crosslinked polymer networks [26][27][28][29][30], organic-inorganic polymer hybrids [31][32][33], surfactants [34], surface modification [35,36] and remendable selfhealing polymers [37]. Due to the fact that these reactions can proceed under mild conditions without a catalyst, they are attractive for designing covalently reversible bonds with furan and maleimide functional groups which are responsible for association and disassociation [35,37,38]. Polyurethanes are widely used in high resiliency flexible foam seating, rigid foam insulation panels, microcellular foam seals and gaskets, durable elastomeric wheels and tires, automotive suspension bushings, electrical potting components, high performance adhesives, surface coatings and sealants, Spandex fibers, seals, gaskets, carpet underlay, and hard plastic parts (such as for electronic instruments).…”

Section: Introductionmentioning

confidence: 99%

Thermally reversible cross-linked poly(ether-urethane)s

Găină¹,

Ursache²,

Gaina³

et al. 2013

Express Polym. Lett.

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Abstract. Cross-linked poly(ether-urethane)s were prepared by Diels-Alder (DA) reaction of the furan-containing poly(ether-urethane) to bismaleimides and showed thermal reversibility evidenced by differential scanning calorimetry and attenuated total reflectance in conjunction with Fourier transform infrared spectroscopy (ATR-FTIR). The furan-containing poly(ether-urethane)s were synthesized by the polyaddition reaction of 1,6-hexamethylene diisocyanate (HMDI) or 4,4!-dibenzyl diisocyanate (DBDI) to poly(tetramethylene ether) glycol (PTMEG having M n = 250, 650, 1000, 1500 and 2000) and 2-[N,N-bis(2-methyl-2-hydroxyethyl)amino]furfuryl as chain extender by the solution prepolymer method. The molar ratio of isocyanate: PTMEG:chain extender varied from 2:1:1 to 4:1:3, which produces a molar concentration of furyl group ranging between 3.65·10 -4 and 1.25·10 -3 mol/g.

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Section: Introductionmentioning

confidence: 99%

Thermally reversible cross-linked poly(ether-urethane)s

Găină¹,

Ursache²,

Gaina³

et al. 2013

Express Polym. Lett.

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“…Zhu et al [77] reported an approach for the derivatization of monolayer-protected nanoparticle (MPNs) surfaces with a reactive maleimide entity using the thermally reversible DA reaction of furan with a maleimide. These authors showed that by preparing a surface with a furan-maleimide adduct, it is possible to efficiently generate, reversibly, a maleimide-modified MPN via a thermally induced retro-DA reaction.…”

Section: Gold and Metal-based Nanoparticlesmentioning

confidence: 99%

Orthogonal Transformations on Solid Substrates: Efficient Avenues to Surface Modification

2009

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The performance of solid substrates is not only governed by their molecular constitution, but is also critically influenced by their surface constitution at the solid/gas or solid/liquid interface. In here, we critically review the use of orthogonal chemical transformations (so‐called click chemistry) to achieve efficient surface modifications of materials ranging from gold and silica nanoparticles, polymeric films, and microspheres to fullerenes as well as carbon nanotubes. In addition, the functionalization of surfaces via click chemistry with biomolecules is explored. Although a large host of reactions fulfilling the click‐criteria exist, pericyclic reactions are most frequently employed for efficient surface modifications. The advent of the click chemistry concept has led—as evident from the current literature—to a paradigm shift in current approaches for materials modification: Away from unspecific and nonselective reactions to highly specific true surface engineering.

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“…23 The same is true for CS, which is a predominant component of the extracellular matrix and meets both structural and biological requirements for biomaterials synthesis. 26 However, to the best of our knowledge, this is the rst time that hybrid hydrogels were prepared by Diels-Alder reaction using Au NPs as cross-linkers for gelatin chains. 24 Additionally, second cross-linking, based on the amide coupling between CS and gelatin was employed to stabilize the hydrogel.…”

Section: Introductionmentioning

confidence: 96%

Effect of maleimide-functionalized gold nanoparticles on hybrid biohydrogels properties

et al. 2015

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The role of well-dispersed gold nanoparticles as cross-linking agents in nanocomposite hydrogel formation was studied. Maleimide-coated gold nanoparticles were synthesized and used for Diels-Alder cycloaddition with furan modified gelatin. Hydrogel formation was aided by additional amide coupling of the modified gelatin with chondroitin sulfate. The cross-linking ability of the functionalized nanoparticles was evaluated and the final hydrogel properties were compared to those of a hybrid hydrogel containing inert-linker coated gold nanoparticles. The storage modulus of the nanoparticle cross-linked nanocomposites was 2.5-3 times compared to the controls. The presence of nanoparticles also affected the swelling properties, resulting in lower swelling ratios due to the formation of the more cross-linked structures. Conducted drug delivery experiments and the study of the light irradiation on the drug release behavior revealed promising features for the applications of nanocomposite polymer for drug delivery.Scheme 3 Hydrogel formation reactions; path (a) amide coupling between CS and Gel-FGE in the presence of EDC and NHS and path (b) DA reaction between G-FGE and maleimide-coated Au NPs.This journal is

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A Retro-Diels−Alder Reaction to Uncover Maleimide-Modified Surfaces on Monolayer-Protected Nanoparticles for Reversible Covalent Assembly

Cited by 47 publications

References 25 publications

Thermally reversible cross-linked poly(ether-urethane)s

Thermally reversible cross-linked poly(ether-urethane)s

Orthogonal Transformations on Solid Substrates: Efficient Avenues to Surface Modification

Effect of maleimide-functionalized gold nanoparticles on hybrid biohydrogels properties

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