Reversible addition–fragmentation chain transfer step-growth polymerization with commercially available inexpensive bis-maleimides

Boeck, Parker T.; Archer, Noel; Tanaka, Joji; You, Wei

doi:10.1039/d2py00236a

Cited by 14 publications

(33 citation statements)

References 39 publications

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“…This important insight was first investigated by McLeary and Klumperman, − and independently confirmed by Chen and Ghiggino with stoichiometric ratio of monomer to CTA. , Taking advantage of the RAFT-SUMI cycle, we recently reported RAFT step-growth polymerization by using bifunctional reagents bearing CTA and monomer functionalities that yield high SUMI-CTA adducts . RAFT step-growth polymerization synergistically combines the desirable features of both RAFT (functional group tolerance and user-friendly nature) and step-growth (functional backbone). , Shortly after, Li and Zhu independently reported a catalyst-free, photomediated RAFT step-growth …”

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confidence: 80%

“…14 RAFT step-growth polymerization synergistically combines the desirable features of both RAFT (functional group tolerance and user-friendly nature) and step-growth (functional backbone). 14,15 Shortly after, Li and Zhu independently reported a catalyst-free, photomediated RAFT step-growth. 16 Figure 1A outlines the proposed mechanism of RAFT stepgrowth polymerization.…”

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confidence: 99%

“…However, branching would occur if R-M • reacts with additional monomer species, which is dictated by the homopolymerization rate of the monomer ( k p ). To limit this occurrence, monomers with low k p were chosen (maleimides and vinyl ether) in previous reports to promote chain transfer cycle. − To date, more reactive monomers such as acrylates that bear high k p have never been explored for RAFT step-growth polymerization.…”

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confidence: 99%

“…As CTA 1C demonstrated high SUMI-CTA adduct yields with BA in our model RAFT SUMI study, CTA 2 was prepared following our previous report. , 1,6-hexanediol diacrylate ( M 2A ) was chosen as our initial model diacrylate monomer to match the linker length with CTA 2 . RAFT step-growth polymerization was carried out in 2 M concentration of the monomer functional groups in 1,4-dioxane using stoichiometrically equivalent CTA 2 and initiated using AIBN at 70 °C.…”

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RAFT Step-Growth Polymerization of Diacrylates

et al. 2022

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RAFT step-growth polymerization was previously demonstrated with monomers that bear low rate of homopropagation to favor the chain transfer process; by contrast, acrylates are known to be fast homopropagating monomers, thereby posing serious challenges for RAFT step-growth. Here, we identified a chain transfer agent (CTA) that rapidly yields single unit monomer inserted (SUMI) CTA adducts with a model acrylate monomer. Using a bifunctional reagent of this CTA, we successfully demonstrated RAFT step-growth polymerization with diacrylates, yielding linear polymer backbones. Furthermore, we achieved inclusion of functionality (i.e., disulfide) into RAFT step-growth polymer via a disulfide incorporated bifunctional CTA. Grafting from this backbone resulted in molecular brush polymers with cleavable functionality in each repeat unit of the backbone, allowing selective degradation to afford well-defined unimolecular species of two polymeric side chains. Given the wide selection of commercially available diacrylates, RAFT step-growth polymerization of diacrylates will further enable facile synthesis of complex architectures with modular backbones.

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RAFT Step-Growth Polymerization of Diacrylates

et al. 2022

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“…Many commercially available bismaleimide-derivatives of resin are reported due to their simple industrial synthesis and cheap raw materials [21,22]. Many studies have investigated enhancing the physical properties of BMI in order to design reactive functional groups or rigid moieties into the BMI monomers, which could also incorporate inorganic nanoparticles such as POSS, graphene, or carbon nanotubes [23][24][25][26][27][28][29].…”

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Double-Decker-Shaped Polyhedral Silsesquioxanes Reinforced Epoxy/Bismaleimide Hybrids Featuring High Thermal Stability

Chen

Ba³

et al. 2022

Polymers

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In this study, we synthesized bismaleimide into a functionalized double-decker silsesquioxane (DDSQ) cage. This was achieved by hydrosilylation of DDSQ with nadic anhydride (ND), reacting it with excess p-phenylenediamine to obtain DDSQ-ND-NH2, and treating with maleic anhydride (MA), which finally created a DDSQ-BMI cage structure. We observed that the thermal decomposition temperature (Td) and char yield were both increased upon increasing the thermal polymerization temperature, and that these two values were both significantly higher than pure BMI without the DDSQ cage structure since the inorganic DDSQ nanoparticle could strongly enhance the thermal stability based on the nano-reinforcement effect. Based on FTIR, TGA, and DMA analyses, it was found that blending epoxy resin with the DDSQ-BMI cage to form epoxy/DDSQ-BMI hybrids could also enhance the thermal and mechanical properties of epoxy resin due to the organic/inorganic network formation created by the ring-opening polymerization of the epoxy group and the addition polymerization of the BMI group due to the combination of the inorganic DDSQ cage structure and hydrogen bonding effect. The epoxy/DDSQ-BMI = 1/1 hybrid system displayed high Tg value (188 °C), Td value (397 °C), and char yield (40.4 wt%), which was much higher than that of the typical DGEBA type epoxy resin with various organic curing agents.

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Tuning the Mechanical Properties of 3D‐printed Objects by the RAFT Process: From Chain‐Growth to Step‐Growth

Pan,

Li,

et al. 2024

Angewandte Chemie

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Photoinduced 3D printing based on the reversible addition‐fragmentation chain transfer (RAFT) process has emerged as a robust method for creating diverse functional materials. However, achieving precise control over the mechanical properties of these printed objects remains a critical challenge for practical application. Here, we demonstrated a RAFT step‐growth polymerization of a bifunctional xanthate and bifunctional vinyl acetate. Additionally, we demonstrated photoinduced 3D printing through RAFT step‐growth polymerization with a tetrafunctional xanthate and a bifunctional vinyl acetate. By adjusting the molar ratio of the components in the printing resins, we finely tuned the polymerization mechanism from step‐growth to chain‐growth. This adjustment resulted in a remarkable range of tunable Young’s moduli, ranging from 7.6 MPa to 997.1 MPa. Moreover, post‐functionalization and polymer welding of the printed objects with varying mechanical properties opens up a promising way to produce tailor‐made materials with specific and tunable properties.

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Reversible addition–fragmentation chain transfer step-growth polymerization with commercially available inexpensive bis-maleimides

Abstract: Here, commercially available N-aromatic substituted bismaleimides were used in RAFT step-growth polymerization for the first time. In our initial report (J. Am. Chem. Soc. 2021, 143 (39), 15918-15923), maleimide precursors...

Cited by 14 publications

References 39 publications

RAFT Step-Growth Polymerization of Diacrylates

RAFT Step-Growth Polymerization of Diacrylates

Double-Decker-Shaped Polyhedral Silsesquioxanes Reinforced Epoxy/Bismaleimide Hybrids Featuring High Thermal Stability

Tuning the Mechanical Properties of 3D‐printed Objects by the RAFT Process: From Chain‐Growth to Step‐Growth

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