The furan/maleimide Diels–Alder reaction: A versatile click–unclick tool in macromolecular synthesis
The purpose of this review is to provide a critical survey covering a few decades of growing interest in the application to polymer chemistry of the Diels–Alder (DA) reaction between furan and maleimide moieties. The major peculiarity of this specific combination of reagents is the fact that their c...
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| Published in | Progress in polymer science Vol. 38; no. 1; pp. 1 - 29 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Kidlington
Elsevier Ltd
01.01.2013
Elsevier |
| Subjects | |
| Online Access | Get full text |
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| Abstract | The purpose of this review is to provide a critical survey covering a few decades of growing interest in the application to polymer chemistry of the Diels–Alder (DA) reaction between furan and maleimide moieties. The major peculiarity of this specific combination of reagents is the fact that their click coupling to generate the DA adduct is thermally reversible, through the retro-DA reaction, at about 100°C, i.e., a viable and non-degradative temperature in terms of its application to practically all macromolecular structures. The use of furan derivatives constitutes an additional positive feature in this context, because of their renewable character. Attempts were made to insure a comprehensive coverage of the literature, which deals with vastly different approaches and aims concerning the chemistry, the polymer architectures and the possible application of the ensuing materials. The decision to cite all publications available on the subject was deliberate in the sense that in doing so, it was possible to examine them critically and highlight excellence and flaws. |
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| AbstractList | The purpose of this review is to provide a critical survey covering a few decades of growing interest in the application to polymer chemistry of the Diels–Alder (DA) reaction between furan and maleimide moieties. The major peculiarity of this specific combination of reagents is the fact that their click coupling to generate the DA adduct is thermally reversible, through the retro-DA reaction, at about 100°C, i.e., a viable and non-degradative temperature in terms of its application to practically all macromolecular structures. The use of furan derivatives constitutes an additional positive feature in this context, because of their renewable character. Attempts were made to insure a comprehensive coverage of the literature, which deals with vastly different approaches and aims concerning the chemistry, the polymer architectures and the possible application of the ensuing materials. The decision to cite all publications available on the subject was deliberate in the sense that in doing so, it was possible to examine them critically and highlight excellence and flaws. The purpose of this review is to provide a critical survey covering a few decades of growing interest in the application to polymer chemistry of the Diels-Alder (DA) reaction between furan and maleimide moieties. The major peculiarity of this specific combination of reagents is the fact that their click coupling to generate the DA adduct is thermally reversible, through the retro-DA reaction, at about 100 degree C, i.e., a viable and non-degradative temperature in terms of its application to practically all macromolecular structures. The use of furan derivatives constitutes an additional positive feature in this context, because of their renewable character. Attempts were made to insure a comprehensive coverage of the literature, which deals with vastly different approaches and aims concerning the chemistry, the polymer architectures and the possible application of the ensuing materials. The decision to cite all publications available on the subject was deliberate in the sense that in doing so, it was possible to examine them critically and highlight excellence and flaws. |
| Author | Gandini, Alessandro |
| Author_xml | – sequence: 1 givenname: Alessandro surname: Gandini fullname: Gandini, Alessandro email: agandini@iqsc.usp.br organization: Instituto de Química and Escola de Engenharia de São Carlos, Universidade de São Paulo, 13566-590 São Carlos, Brazil |
| BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26785736$$DView record in Pascal Francis |
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| Keywords | Cyclic crosslinking/decrosslinking Furans Click chemistry Thermoreversible polymerizations Maleimides Diels–Alder reaction Polyimide Cyclopolymerization Furan derivatives Diels Alder addition Reversible reaction Review Chemical modification Maleimide derivative polymer Diels-Alder reaction |
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| SubjectTerms | Applied sciences chemistry Click chemistry Copolymerization Cyclic crosslinking/decrosslinking Defects Derivatives Diels-Alder reactions Diels–Alder reaction Exact sciences and technology Furans Joining Maleimides Organic polymers Physicochemistry of polymers Polymer chemistry polymers Preparation, kinetics, thermodynamics, mechanism and catalysts surveys Synthesis temperature Thermoreversible polymerizations |
| Title | The furan/maleimide Diels–Alder reaction: A versatile click–unclick tool in macromolecular synthesis |
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