Thermally stable recyclable naphthalenediimide–siloxane polymers

Prentice, Giles M.; Emmett, Liam; Zhu, Huiling; Kociok‐Köhn, Gabriele; Pantoş, G. Dan

doi:10.1080/10610278.2015.1117085

Cited by 3 publications

(5 citation statements)

References 21 publications

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“…Briefly, to synthesize Lap-PDI4O, a symmetric tetraethyleneglycol-substituted perylene diimide (PDI4O) was first synthesized according to the method described by Traeger et al Perylene-3,4,9,10-tetracarboxylic acid dianhydride was reacted with tetraethyleneglycol monoamine in dry DMF. In the next step, tetraethyleneglycol perylene monoimide (PMI4O) was synthesized through partial hydrolysis of tetraethyleneglycol perylene diimide (PDI4O) with potassium hydroxide. , Finally, PMI4O was reacted with aminopropyldimethylethoxysilane-modified Lap (Lap-APES), yielding the hybrid Lap-PDI4O. , To synthesize Lap-NDI2O, naphthalene diglycol monoimide (NMI2O) was first synthesized from naphthalene tetracarboxylic acid dianhydride according to the method described by Imato et al In the next step, NMI2O was reacted with Lap-APES to form Lap-NDI2O following a modification of the method by Prentice et al Detailed synthetic methods and characterization details are given in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

“…31,32 Finally, PMI4O was reacted with aminopropyldimethylethoxysilane-modified Lap (Lap-APES), yielding the hybrid Lap-PDI4O. 19,33 To synthesize Lap-NDI2O, naphthalene diglycol monoimide (NMI2O) was first synthesized from naphthalene tetracarboxylic acid dianhydride according to the method described by Imato et al 34 In the next step, NMI2O was reacted with Lap-APES to form Lap-NDI2O following a modification of the method by Prentice et al 35 Detailed synthetic methods and characterization details are given in the Supporting Information.…”

Section: ■ Methodsmentioning

confidence: 99%

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2D Nanomaterial-Directed Molecular Aggregation and Energy Transfer between Edge-Bound Donor–Acceptor Pairs

Xiang,

Valandro,

Hill

2023

J. Phys. Chem. C

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Forster resonance energy transfer (FRET) is a phenomenon that is observed between an excited energy donor and ground-state acceptor in close proximity. The efficiency of FRET varies with the distance and orientation of the donor−acceptor pair, solvent, and other competing processes. Layered silicates, with their ability to stack in "pillars" with a certain interlayer spacing, present a useful platform to influence the interactions of edge-bound groups. In this study, asymmetric perylene and naphthalene diimides were grafted to the edge of the layered silicate Laponite, and their photophysical properties and aggregation behavior were studied in different compositions of water and dimethylformamide. FRET was observed from naphthalene diimide-to perylene diimide-functionalized Laponite, and pillaring of Laponite with a cationic surfactant led to significantly enhanced FRET, which was attributed to the reorientation of chromophores due to the organized stacking of pillared particles. This study reports how ordering of the discoidal layered silicate nanoparticles into organized stacks can tune the aggregation of edge-bound FRET pairs. This can aid in understanding donor−acceptor interactions at the interface of anisotropic nanomaterials and improve control over the distance and orientation of donor−acceptor pairs and resulting energy transfer processes. Furthermore, this is the first example of the attachment of naphthalene diimides to layered silicate edge sites. This study opens the door to further studies of geometry-dependent energy flows in inorganic−organic hybrid materials and will advance applications in sensing, energy, and molecular electronics.

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Section: Methodsmentioning

confidence: 99%

Section: ■ Methodsmentioning

confidence: 99%

2D Nanomaterial-Directed Molecular Aggregation and Energy Transfer between Edge-Bound Donor–Acceptor Pairs

Xiang,

Valandro,

Hill

2023

J. Phys. Chem. C

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“… The cyclic voltammetry of the dyad showed two large quasi-reversible reduction waves at −1.0 and −1.5 V, respectively, and the reversible oxidation of the ruthenium center was detected around +0.5 V. In this dyad, the long-lived excited state of the ruthenium center photosensitizer is exploited to promote efficient charge separation irrespective of the flexible saturated linkage pattern. Prentice et al reported the synthesis and characterization of another NDI-based polymer that is polymerized using the N-substitution moieties . They synthesized a NDI–siloxane series of recyclable polymers (495–498) with high thermal stability.…”

Section: Optical Properties and Optoelectronicsmentioning

confidence: 99%

“…Prentice et al reported the synthesis and characterization of another NDI-based polymer that is polymerized using the N-substitution moieties. 548 They synthesized a NDI−siloxane series of recyclable polymers (495−498) with high thermal stability. These polymers also showed self-healing properties due to the combination of the simple acid−base-triggered repair system, making them strong candidates for flexible electronic devices.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

et al. 2016

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This comprehensive review surveys developments over the past decade in the field of naphthalene diimides (NDIs). It explores their application toward: supramolecular chemistry; sensors; host-guest complexes for molecular switching devices, such as catenanes and rotaxanes; ion-channels by ligand gating; gelators for sensing aromatic systems; catalysis through anion-π interactions; and NDI intercalations with DNA for medicinal applications. We have also explored new designs, synthesis, and progress in the field of core-substituted naphthalene diimides (cNDIs), and their implications in areas such as artificial photosynthesis and solar cell technology. Also presented are some interesting synthetic routes and procedures that can be used toward further development of NDI-bearing compounds for future applications. Finally, we conclude with our views on NDI chemistry for future research endeavors, and we outline what we believe are the key obstacles that need to be overcome for NDIs to see real world applications.

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“…22 Simultaneously, the formation of a complex electron transfer between the siloxane and the polyimide improved the energy barrier of degradation and enhanced the coupling of the macromolecule thermal stability. 23 Adjusting the ratio of the two diamines also brought more designability to the structure of the macromolecular coupling agent. The side group -Si (OC 2 H 5 ) 3 in this macromolecular coupling agent may react with the -OH group on the QF surface, and the terminal alkyne in the main chain will react with the matrix.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermal stability of a novel acetylene end-capped silicon-containing polyimide coupling agent with a silane pendant group

Yang

Deng

et al. 2019

High Performance Polymers

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In this study, a novel heat-resistant polyimide macromolecular coupling agent (PSI-C) was designed and synthesized. Silicon-containing diamine was one of the monomers used to increase the solubility of the polyimide, and m-aminophenylacetylene was the end-capping reagent that copolymerized with the resin matrix. A silane coupling group was introduced into the side chain to match the reinforced fiber. Thermogravimetric analysis revealed that the 5% thermal decomposition temperature ( T d5) of the cured PSI-C could reach 454°C and the residual rate at 800°C was 53%. Thermal pyrolysis of the vaporized resin showed that the heat-resistant functional group was still detectable at 550°C. The thermal stability of the alkynyl-terminated silicon-containing polyimide silane coupling agent was higher than those of conventional silane coupling agents. The curing process of the composite system was not affected when adding the coupling agent PSI-C to the quartz fiber/alkynyl resin composite. The interlaminar shear strength and bending strength of the composite were increased by 55% and 61%, respectively, at room temperature. The high-temperature retention rate at 500°C reached 58% and 63%.

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Thermally stable recyclable naphthalenediimide–siloxane polymers

Cited by 3 publications

References 21 publications

2D Nanomaterial-Directed Molecular Aggregation and Energy Transfer between Edge-Bound Donor–Acceptor Pairs

2D Nanomaterial-Directed Molecular Aggregation and Energy Transfer between Edge-Bound Donor–Acceptor Pairs

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

Synthesis and thermal stability of a novel acetylene end-capped silicon-containing polyimide coupling agent with a silane pendant group

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