Elastomers built up through the π–π stacking association of polycyclic planar aromatic diimides

Higaki, Yasuki; Kiyoshima, Yudai; Suzuki, Ken; Kabayama, Hirofumi; Ohta, Nobuhiro; Seo, Yongsok; Takahara, Atsushi

doi:10.1039/c7ra08910d

Cited by 10 publications

(8 citation statements)

References 32 publications

(31 reference statements)

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“…Furthermore, the polymers have an endothermic transition at 129 °C (P1) and 126 °C (P2). This transition is associated with the activation of the perylene domains, which was also reported in literature [23]. During cooling, the reformation of the perylene domain was also observed.…”

Section: Characterization Of the Polymerssupporting

confidence: 82%

“…For the synthesis of supramolecular polymers based on π-π interactions a literature reported procedure was utilized (see Scheme 1 ), which described the synthesis of polypropylene glycol-based polymers featuring aromatic diimides [ 23 ]. Following the procedure, perylene-3,4,9,10-tetracarboxylic dianhydride was converted with poly(propylene glycol) bis(2-aminopropyl ether) with a molar mass of approximately 2000 g/mol resulting in polymer P1 .…”

Section: Resultsmentioning

confidence: 99%

“…The polymer synthesis was adapted from literature [23] and is reported briefly in the following. 39 mmol) were mixed in a round bottom flask under nitrogen atmosphere.…”

Section: Polymer Synthesismentioning

confidence: 99%

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In-depth characterization of self-healing polymers based on π–π nteractions

Meurer¹,

Hniopek²,

Ahner³

et al. 2021

Beilstein J. Org. Chem.

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The self-healing behavior of two supramolecular polymers based on π–π-interactions featuring different polymer backbones is presented. For this purpose, these polymers were synthesized utilizing a polycondensation of a perylene tetracarboxylic dianhydride with polyether-based diamines and the resulting materials were investigated using various analytical techniques. Thus, the molecular structure of the polymers could be correlated with the ability for self-healing. Moreover, the mechanical behavior was studied using rheology. The activation of the supramolecular interactions results in a breaking of these noncovalent bonds, which was investigated using IR spectroscopy, leading to a sufficient increase in mobility and, finally, a healing of the mechanical damage. This scratch-healing behavior was also quantified in detail using an indenter.

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Section: Characterization Of the Polymerssupporting

confidence: 82%

Section: Resultsmentioning

confidence: 99%

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In-depth characterization of self-healing polymers based on π–π nteractions

Meurer¹,

Hniopek²,

Ahner³

et al. 2021

Beilstein J. Org. Chem.

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“…The flexural strength of cured resin is high, which could be possibly attributed to irregular substituted aromatic ether structure and conjugated naphthalene rings. 22,23 In addition, the storage modulus of m -PPNSA-MM-C first decreased and then increased due to mobilities of chains and thermal crosslinking reactions at a high temperature in Figure 7. The loss factor (tan δ) of m -PPNSA-MM-C is low below 0.16 in the range of 50–400°C, which illustrates that the cured resin has no glass transition below 400°C.…”

Section: Resultsmentioning

confidence: 98%

A high-performance silicon-containing arylacetylene resin with conjugated naphthalene rings

Liu

et al. 2021

High Performance Polymers

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2,7-Diphenyloxynaphthalene with large conjugated structure has been introduced into the main chain of silicon-containing arylacetylene resin and then poly(dimethylsilylene-ethynylenephenoxynaphthyloxyphenylene-ethynylene) ( m-PPNSA-MM) was synthesized. The m-PPNSA-MM resin shows good solubility and a wide processing window. A stable three-dimensional cross-linking network formed due to thermal crosslinking reactions of acetylene groups and intermolecular π–π stacking interactions after m-PPNSA-MM was cured through the process of 180°C/2 h + 220°C/2 h + 260°C/4 h. The flexural strength and modulus of the cured m-PPNSA-MM resin at room temperature are 49.2 MPa and 2.75 GPa, respectively. The cured m-PPNSA-MM resin show high thermal stabilities, the 5% temperature of weight loss ( Td5) reaches 560°C in nitrogen.

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“…When the dimer was employed as an additive in donor:acceptor blends for OPVs, the thermal stability of the device was enhanced . For PDI-based materials, the effect of different alkyl chains on the PDI molecule was investigated in terms of self-assembly , and optoelectronic properties. − Non-conjugated PDI-based polymers were also investigated and used in all polymer solar cells as non-fullerene acceptors …”

Section: Introductionmentioning

confidence: 99%

A “Rigid–Flexible” Approach for Processable Perylene Diimide-Based Polymers: Influence of the Specific Architecture on the Morphological, Dielectric, Optical, and Electronic Properties

et al. 2020

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Conjugation-break flexible spacers in-between πconjugated segments were utilized herein toward processable perylene diimide (PDI)-based polymers. Aromatic−aliphatic PDIbased polymers were developed via the two-phase polyetherification of a phenol-difunctional PDI monomer and aliphatic dibromides. These polyethers showed excellent solubility and filmforming ability and deep lowest unoccupied molecular orbital (LUMO) levels (−4.0 to −3.85 eV), indicating the preservation of good electron-accepting character or characteristics, despite the non-conjugated segments. Their thermodynamic properties, local dynamics, and ionic conductivity demonstrate the suppression of PDI's inherent tendency for aggregation and crystallization, suggesting PDI-polyethers as versatile candidates for organic electronic applications. Their dynamics investigation using dielectric spectroscopy revealed weak dipole moments arising from the distortion of the planar perylene cores. Blends of the PDI-polyethers (as electron acceptors) with P3HT (as a potential electron donor component) showed UV−vis absorbances from 350 to 650 nm and a tendency of the PDI-polyethers to intertwine with rr-P3HT and restrain its high crystallization tendency.

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Elastomers built up through the π–π stacking association of polycyclic planar aromatic diimides

Abstract: Polymers composed of polycyclic aromatic planar diimide (PCAD) units and flexible rubbery poly(propylene glycol) (PPG) chains were synthesized, and the morphology and viscoelasticity were investigated.

Cited by 10 publications

References 32 publications

In-depth characterization of self-healing polymers based on π–π nteractions

In-depth characterization of self-healing polymers based on π–π nteractions

A high-performance silicon-containing arylacetylene resin with conjugated naphthalene rings

A “Rigid–Flexible” Approach for Processable Perylene Diimide-Based Polymers: Influence of the Specific Architecture on the Morphological, Dielectric, Optical, and Electronic Properties

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