Thermally Reversible IPN Organic−Inorganic Polymer Hybrids Utilizing the Diels−Alder Reaction

Imai, Yusuke; Itoh, Hideaki; Naka, Kensuke; Chujo, Yoshiki

doi:10.1021/ma991899b

Cited by 177 publications

(130 citation statements)

References 16 publications

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“…In addition, we achieved control of homogeneity of the polymer hybrids by heat with DielsAlder (DA) reaction. 60,61 Furan-modified polystyrene (PS-F), maleimidemodified alkoxysilane (M-TEOS), and TEOS were used to prepare the polymer hybrid. The DA reaction of maleimide groups and furan groups proceeded at ambient temperature and the retro-DA (RDA) reaction took place on heating.…”

Section: Resultsmentioning

confidence: 99%

Creative Synthesis of Organic–Inorganic Molecular Hybrid Materials

Gon

Tanaka

Chujo

2017

Bulletin of the Chemical Society of Japan

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This manuscript describes a series of our research based on the concept of an organicinorganic molecular hybrid material. Homogeneous organicinorganic hybridization is accomplished by mixing organic components and inorganic ones at a molecular level. Based on the strategy, a great number of hybrid materials have been synthesized and brand-new properties have been developed. Organicinorganic hybrid materials insure the realization of the collaboration of organic features and inorganic features. We recently suggested a new concept of organic inorganic hybrid materials named 'element-blocks'. This concept provides the idea that an element-level design and combinations of the functional units can create innovative materials. Herein, we demonstrate synthetic methods and examples of the organicinorganic hybrid materials, and we introduce our recent work based on the concept of element-blocks.

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Section: Resultsmentioning

confidence: 99%

Creative Synthesis of Organic–Inorganic Molecular Hybrid Materials

Gon

Tanaka

Chujo

2017

Bulletin of the Chemical Society of Japan

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“…[9] Interestingly, there are only a few examples in the literature that involve polymers appended with maleimides towards fabrication of thermoreversible materials. [10] In these studies, maleimides…”

Section: Thermoreversible Crosslinked Materialsmentioning

confidence: 99%

Diels–Alder Cycloaddition‐Cycloreversion: A Powerful Combo in Materials Design

Sanyal

2010

Macro Chemistry & Physics

208

112

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Reactive polymers are increasingly becoming materials of wide interest because they offer solutions to challenges in biomolecular immobilization, drug‐delivery and enzyme modifications. The Diels–Alder (DA) cycloaddition and the retro Diels–Alder (rDA) cycloreversion reaction in combination enables synthesis of maleimide based reactive polymeric materials. Also, the DA cycloaddition offer a reagent‐free ‘click’ reaction to construct various macromolecular architectures. Furthermore, the thermally reversible nature of the DA adducts makes them attractive building blocks for the design of thermoreversible materials. A discussion of some of the author's own research work in this area is presented in this article within the context of recent reports in polymer chemistry employing this reaction combo.magnified image

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“…The DA cycloaddition of furan and maleimide can be accomplished at or slightly above room temperature, while the rDA reaction is performed at elevated temperatures. 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].…”

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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Thermally Reversible IPN Organic−Inorganic Polymer Hybrids Utilizing the Diels−Alder Reaction

Cited by 177 publications

References 16 publications

Creative Synthesis of Organic–Inorganic Molecular Hybrid Materials

Creative Synthesis of Organic–Inorganic Molecular Hybrid Materials

Diels–Alder Cycloaddition‐Cycloreversion: A Powerful Combo in Materials Design

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

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