A recyclable indole-based polymer for trinitrotoluene adsorption<i>via</i>the synergistic effect of dipole–π and donor–acceptor interactions

Wang, Yan; Zhang, Lin; Yang, Li; Ma, Yuanchi

doi:10.1039/c9py00820a

Cited by 19 publications

(10 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to the literature, 30,31 the electron‐deficient imidazolium ions would self‐assemble via “face–face” π–π stacking with the electron‐rich benzene rings. Notably, compared with other “point–point” and “point–face” noncovalent interactions, this “face–face” π–π interaction shares a larger binding area 32–35 . The negatively charged oxygen, on the one hand, can attack another epoxy group to form further chemical crosslinks; on the other hand, it can form a “point–point” hydrogen bond with the OH in the polymer network 36 .…”

Section: Resultsmentioning

confidence: 99%

“…Notably, compared with other "point-point" and "point-face" noncovalent interactions, this "face-face" π-π interaction shares a larger binding area. [32][33][34][35] The negatively charged oxygen, on the one hand, can attack another epoxy group to form further chemical crosslinks; on the other hand, it can form a "point-point" hydrogen bond with the OH in the polymer network. 36 Moreover, the imidazolium cation and negatively charged oxygen anion can also attract each other to self-assemble ion-pair electrostatic interaction.…”

Section: Preparations and Structural Characterizations Of The Rigid T...mentioning

confidence: 99%

See 1 more Smart Citation

Toughening rigid thermoset films via molecular enforced integration of covalent crosslinking and multiple supramolecular interactions

Wang

Zhang

et al. 2021

Journal of Polymer Science

Self Cite

View full text Add to dashboard Cite

Rigid thermosets show great potential application value in several fields; however, enhancing their extensibility without losing the required mechanical strength is always a huge challenge. In this work, a new class of rigid thermosets, poly(triethylenetetramine bisphenol A epoxy phenylimidazole)s, with both multiple supramolecular interactions, including “face–face” π–π stacking, “point–point” hydrogen bond, and ion‐pair electrostatic interaction, and covalent crosslinks is developed by introducing the special functional group 2‐phenylimidazole into the crosslinked thermoset. Owing to the synergistic effect of the strong covalent crosslinks and the multiple supramolecular interactions, synchronously improved tensile strengths and elongation at break have been successfully obtained with these rigid thermosets.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Preparations and Structural Characterizations Of The Rigid T...mentioning

confidence: 99%

Toughening rigid thermoset films via molecular enforced integration of covalent crosslinking and multiple supramolecular interactions

Wang

Zhang

et al. 2021

Journal of Polymer Science

Self Cite

View full text Add to dashboard Cite

show abstract

“…22,23 More importantly, compared with "point-point" and "point-face" noncovalent interactions, the "face-face" interaction possesses a relatively larger binding area. [24][25][26][27] Moreover, according to the literature, the imidazolium cations can also attract other anions to self-assemble ion-pair electrostatic interactions. 28,29 Therefore, in this study, the IMDA was introduced into an octane-1,8-diamine (ODA) crosslinked diglycidyl ether of bisphenol-A epoxy resin (DGEBA) network (Figure 1(a)) to create a hybrid aromatic thermoset network with both covalent crosslink and multiple noncovalent interactions (Figure 1(c)).…”

Section: Assembly and Structural Characterization Of The Aromatic Thermosetsmentioning

confidence: 99%

Simultaneously improving the ductility and strength of aromatic thermoset films

Wang

Zhang

et al. 2021

High Performance Polymers

Self Cite

View full text Add to dashboard Cite

Aromatic thermoset materials have shown great potential applications in various fields owing to their excellent mechanical strengths. However, their poor ductility is still hinders their large-scale applications. In this study, a new class of aromatic thermosets consisting of two types of crosslinks was successfully developed by incorporating the special group imidazole into a type of crosslinked thermoset. One crosslink is constituted of reversible multiple noncovalent interactions containing “face-face” π–π stacking, “point-point” hydrogen bonds, and ion-pair electrostatic interactions, whereas the other is composed of permanent covalent bonds. Most importantly, the synergetic interplay among these reversible multiple noncovalent interactions enables them to evade the restrictions from the aromatic polymer skeletons to proceed with their dynamic dissociating-rebuilding processes, which can timely and effectively dissipate the internal stress. Finally, owing to the coefficient of these two types of crosslinks, a significantly enhanced ductility was successfully obtained on these aromatic thermosets and their tensile strengths were also improved. Such thermosets having simultaneously enhanced strengths and ductility are predicted to be eventually used in a wide range of applications.

show abstract

“…Inspired by the use of local dipole-π interaction to capture carbon dioxide (CO 2 ), 18 Chang et al achieved efficient adsorption of highly polarized TNT through dipole-π interaction. 19 Compared with the traditional point-to-point interactions (hydrogen bond, donor acceptor interaction, etc. ), the point-to-face dipole-π interaction enlarged the binding area between the porous polymer and TNT, making it easier to adsorb TNT, thus shortening the adsorption equilibrium time.…”

Section: Introductionmentioning

confidence: 99%

Efficient adsorption of trinitrotoluene by isoxazoline‐based porous polymers prepared from room‐temperature stable bis(nitrile oxide)

Yang

Deng

et al. 2023

J of Applied Polymer Sci

Self Cite

View full text Add to dashboard Cite

A novel isoxazoline-based porous adsorbent (PB-TTNO) is prepared by click polymerization and freeze-drying from a methyl-containing bis(nitrile oxide) stable at room temperature. The introduction of four methyl groups around the nitrile oxide group reduces the activity of the bis(nitrile oxide) and make it react more mildly with polybutadiene, resulting in PB-TTNO with a more uniform pore size. Meanwhile, the electron-donating methyl groups further increase the π-π interaction between the polymer benzene ring and the TNT benzene ring. The π-π interaction enables one benzene ring in the polymer to interact with two TNT molecules to form a sandwich structure, which further improves the adsorption capacity. The synergistic effect of dual π-π interactions and dipole-π interactions makes the maximum adsorption capacity of PB-TTNO reach 235.3 mg g À1 within 12 h at 25 C. The factors such as pH value, adsorbent dosage, contact time, initial TNT concentration, and temperature are also discussed. The adsorption kinetics fit well with the pseudo-second-order model, and the Langmuir model exhibits better correlation for equilibrium data analysis. In addition, the adsorption data of PB-TTNO in real water samples are similar to those in laboratory, and the maximum adsorption capacity decreases by only 15% after five adsorption-desorption cycles.

show abstract

A recyclable indole-based polymer for trinitrotoluene adsorptionviathe synergistic effect of dipole–π and donor–acceptor interactions

Abstract: A new type of indole-based porous organic polymer with amine units (PAIN) has been constructed, which possesses encouraging and effective adsorption properties for trinitrotoluene by taking advantage of the synergistic effect of dipole–π and donor–acceptor interactions.

Cited by 19 publications

References 40 publications

Toughening rigid thermoset films via molecular enforced integration of covalent crosslinking and multiple supramolecular interactions

Toughening rigid thermoset films via molecular enforced integration of covalent crosslinking and multiple supramolecular interactions

Simultaneously improving the ductility and strength of aromatic thermoset films

Efficient adsorption of trinitrotoluene by isoxazoline‐based porous polymers prepared from room‐temperature stable bis(nitrile oxide)

Contact Info

Product

Resources

About