Chiral Bifunctional Thioureas and Squaramides Grafted into Old Polymers of Intrinsic Microporosity for Novel Applications

Valle, M.; Martin, Laura B.; Maestro, A.; Andrés, José M.; Pedrosa, Rafaël

doi:10.3390/polym11010013

Cited by 12 publications

(14 citation statements)

References 49 publications

(56 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The FTIR analysis showed the reaction among the phenyl isothiocyanate and amine and hydroxyl groups on gelatin backbones ( Figure 2 a). The increased peaks of the FTIR spectrum at 3300, 3180, 1530, and 830 cm −1 related to the symmetric and asymmetric -NH, C–N, and C=S bonds were observed, respectively [ 44 , 45 , 46 ], indicating phenyl isothiocyanate was grafted on the gelatin backbones successfully. A previous study has reported that the methacrylation reaction of gelatin [ 47 ].…”

Section: Resultsmentioning

confidence: 99%

An Injectable Hybrid Gelatin Methacryloyl (GelMA)/Phenyl Isothiocyanate-Modified Gelatin (Gel-Phe) Bioadhesive for Oral/Dental Hemostasis Applications

et al. 2021

View full text Add to dashboard Cite

Biomaterials are widely used for effectively controlling bleeding in oral/dental surgical procedures. Here, gelatin methacryloyl (GelMA) was synthesized by grafting methacrylic anhydride on gelatin backbone, and phenyl isothiocyanate-modified gelatin (Gel-Phe) was synthesized by conjugating different gelatin/phenyl isothiocyanate molar ratios (G/P ratios) (i.e., 1:1, 1:5, 1:10, 1:15, 1:25, 1:50, 1:100, and 1:150) with gelatin polymer chains. Afterward, we combined GelMA and Gel-Phe as an injectable and photo-crosslinkable bioadhesive. This hybrid material system combines photo-crosslinking chemistry and supramolecular interactions for the design of bioadhesives exhibiting a highly porous structure, injectability, and regulable mechanical properties. By simply regulating the G/P ratio (1:1–1:15) and UV exposure times (15–60 s), it was possible to modulate the injectability and mechanical properties of the GelMA/Gel-Phe bioadhesive. Moreover, we demonstrated that the GelMA/Gel-Phe bioadhesive showed low cytotoxicity, a highly porous network, and the phenyl-isothiourea and amine residues on Gel-Phe and GelMA polymers with synergized hemostatic properties towards fast blood absorption and rapid clotting effect. An in vitro porcine skin bleeding and an in vitro dental bleeding model confirmed that the bioadhesive could be directly extruded into the bleeding site, rapidly photo-crosslinked, and reduced blood clotting time by 45%. Moreover, the in situ crosslinked bioadhesive could be easily removed from the bleeding site after clotting, avoiding secondary wound injury. Overall, this injectable GelMA/Gel-Phe bioadhesive stands as a promising hemostatic material in oral/dental surgical procedures.

show abstract

Section: Resultsmentioning

confidence: 99%

An Injectable Hybrid Gelatin Methacryloyl (GelMA)/Phenyl Isothiocyanate-Modified Gelatin (Gel-Phe) Bioadhesive for Oral/Dental Hemostasis Applications

et al. 2021

View full text Add to dashboard Cite

show abstract

“…section 3.6 for chiral PIMs). [23] PIM-1-amidoxime has been reacted with acid chloride to convert it to amidoxime ester. [81] Overall, PSMs on PIM-1 through modification of the nitrile group is a commonly used approach to introduce highly polar and hydrogen-bond forming functionalities.…”

Section: Postsynthetic Modificationsmentioning

confidence: 99%

Polymers of Intrinsic Microporosity Based on Dibenzodioxin Linkage: Design, Synthesis, Properties, and Applications

Seth

Pathak

Gogoi

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

The development of polymers of intrinsic microporosity (PIMs) over the last two decades has established them as a distinct class of microporous materials, which combine the attributes of microporous solid materials and the soluble nature of glassy polymers. Due to their solubility in common organic solvents, PIMs are easily processable materials that potentially find application in membrane-based separation, catalysis, ion separation in electrochemical energy storage devices, sensing, etc. Dibenzodioxin linkage, Tröger's base, and imide bond-forming reactions have widely been utilized for synthesis of a large number of PIMs. Among these linkages, however, most of the studies have been based on dibenzodioxin-based PIMs. Therefore, this review focuses precisely on dibenzodioxin linkage chemistry. Herein, the design principles of different rigid and contorted monomer scaffolds are discussed, as well as synthetic strategies of the polymers through dibenzodioxin-forming reactions including copolymerization and postsynthetic modifications, their characteristic properties and potential applications studied so far. Towards the end, the prospects of these materials are examined with respect to their utility in industrial purposes. Further, the structure-property correlation of dibenzodioxin PIMs is analyzed, which is essential for tailored synthesis and tunable properties of these PIMs and their molecular level engineering for enhanced performances making these materials suitable for commercial usage.

show abstract

“…Among the prepared polymeric catalysts, Cat-28 showed the best enantioselectivity in the model reaction (Scheme 60). 70 Performing organic reactions under the principles of green chemistry is interesting for both academic and industrial purposes. In this context, Dong et al have shown that the reaction of 2 with malononitrile proceeded smoothly in water at 40 °C for 12 hours without any catalyst or additive to afford functionalized 2-amino-2-chromene derivatives 174 (Scheme 61).…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

“…Among the prepared polymeric catalysts, Cat-28 showed the best enantioselectivity in the model reaction (Scheme 60). 70…”

Section: Reaction With Malononitrilementioning

confidence: 99%

The chemistry of 2-hydroxy-β-nitrostyrenes: versatile intermediates in synthetic organic chemistry

Halimehjani

Ghaffari

2023

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Chiral Bifunctional Thioureas and Squaramides Grafted into Old Polymers of Intrinsic Microporosity for Novel Applications

Cited by 12 publications

References 49 publications

An Injectable Hybrid Gelatin Methacryloyl (GelMA)/Phenyl Isothiocyanate-Modified Gelatin (Gel-Phe) Bioadhesive for Oral/Dental Hemostasis Applications

An Injectable Hybrid Gelatin Methacryloyl (GelMA)/Phenyl Isothiocyanate-Modified Gelatin (Gel-Phe) Bioadhesive for Oral/Dental Hemostasis Applications

Polymers of Intrinsic Microporosity Based on Dibenzodioxin Linkage: Design, Synthesis, Properties, and Applications

The chemistry of 2-hydroxy-β-nitrostyrenes: versatile intermediates in synthetic organic chemistry

Contact Info

Product

Resources

About