Polymer Synthesis via a Diels–Alder Reaction between Bis(Isobenzofuran)s and Bis(Phenylacetylene)s Containing Preformed Phthalimide Rings

Watson, Kent A.; Bass, R. G.

doi:10.1088/0954-0083/12/2/305

Cited by 7 publications

(5 citation statements)

References 27 publications

(32 reference statements)

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“…While there is clear evidence of polymer formation in the reactions of 2 with bis(dienophile)s, we have not attempted to isolate or characterize any of these materials. Similar polymers have been reported and the potential utility of 2 has been mentioned in this context …”

supporting

confidence: 81%

Naphtho[1,2-c:5,6-c]difuran: A Reactive Linker and Cyclophane Precursor

et al. 2003

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Naphtho[1,2-c:5,6-c]difuran has been isolated in a 9-step synthesis from 2,6-dimethylnaphthalene. It is a highly reactive diene similar in nature to the related isobenzofuran. In Diels-Alder reactions, its intermediate monoadducts are actually less reactive that the parent difuran making possible sequential Diels-Alder reactions with different dienophiles. Reaction with a tethered bis(dienophile) leads to the production of a naphthalenic cyclophane.

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supporting

confidence: 81%

Naphtho[1,2-c:5,6-c]difuran: A Reactive Linker and Cyclophane Precursor

et al. 2003

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“…Therefore, the DA reaction may occur first and take the dominant position, which is consistent with the report EDDA has low reactivity. 26,29,30 The lower yield of deoxygenation product (b) might be due to stabilizing influence of electron-withdrawing carbonyl groups on DA Scheme 1 Synthesis of BABF. adduct (a).…”

Section: Heating Process a 250°c For 1 H 280°c For 1 H 280°c For 4 Hmentioning

confidence: 99%

Polyimides from 2,5-bis[4-(4-aminophenoxy)benzoyl]furan and their thermal crosslinking reaction

Jiang

Chen

et al. 2021

High Performance Polymers

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Several polyimides were prepared via two-step polycondensation from novel 2,5-furandicarboxylic acid–based diamine, 2,5-bis[4-(4-aminophenoxy)benzoyl]furan, with commercial dianhydrides. The chemical structures of the monomers and polymers were characterized by FT-IR and NMR in detail, respectively. The polyimides exhibited high performances with 5 wt% weight loss temperatures of over 410 oC, glass transition temperatures of over 214 oC, and tensile strengths and Young’s moduli of up to 130 MPa and 3.2 GPa, respectively. The thermal crosslinking mechanism was studied by FT-IR, Raman spectroscopy, and model reaction analysis, which showed the Diels–Alder reaction between the furan group and diphenylethylene group was the main reaction. The crosslinked polyimide films showed improved solvent resistance, and thermal and mechanical properties.

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“…Diels–Alder reactions have been used in polymer synthesis as a method of producing highly cross‐linked structures15–18 and even as the polymerization mechanism itself 19, 20. It has only been rather recently that it has been effectively utilized in the modular construction of precisely defined polymeric materials.…”

Section: Raft‐hda Chemistrymentioning

confidence: 99%

Ultra Rapid Approaches to Mild Macromolecular Conjugation

Inglis

Barner‐Kowollik

2010

Macromol. Rapid Commun.

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In light of the increasing demand for ultra rapid and mild conjugation chemistries for use in macromolecular chemistry, the present Feature Article provides a critical overview of the very latest developments in this field. The principal aim, therefore, is the provision of a quick selection guide to aid in the formulation of a design strategy for novel functional materials and to provide recommendations for future developments in the chemistries discussed.

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Polymer Synthesis via a Diels–Alder Reaction between Bis(Isobenzofuran)s and Bis(Phenylacetylene)s Containing Preformed Phthalimide Rings

Cited by 7 publications

References 27 publications

Naphtho[1,2-c:5,6-c]difuran: A Reactive Linker and Cyclophane Precursor

Naphtho[1,2-c:5,6-c]difuran: A Reactive Linker and Cyclophane Precursor

Polyimides from 2,5-bis[4-(4-aminophenoxy)benzoyl]furan and their thermal crosslinking reaction

Ultra Rapid Approaches to Mild Macromolecular Conjugation

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