Macromolecular engineering in functional polymers via ‘click chemistry’ using triazolinedione derivatives

Mondal, Prantik; Behera, Prasanta Kumar

doi:10.1016/j.progpolymsci.2020.101343

Cited by 28 publications

(16 citation statements)

References 207 publications

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“…The 1,2,4-triazoline-3,5-diones (triazolinediones, TADs) are highly reactive electrophile reagents with an ample spectra of applications such as Alder-ene cycloadditions, electrophilic aromatic substitution, 2 + 2 and Diels–Alder (DA) cycloadditions, as well as in polymer chemistry and click chemistry. , Focusing on the DA reactions, TADs can react quantitatively with a variety of dienes at low temperatures without a catalyst. Structurally, TADs resemble the more common maleimide dienophiles, the only difference being the presence of a −NN– double bond instead of a −HCCH–.…”

Section: Introductionmentioning

confidence: 99%

Rationalizing the Substituent Effects in Diels–Alder Reactions of Triazolinediones with Anthracene

2022

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In this work we tackle the problem of the substituent effects in the Diels–Alder cycloadditions between triazolinediones (TADs) and anthracene. Experiments showed that aryl TADs substituted with electron-withdrawing groups (EWG) are more reactive than those substituted with electron-donating (EDG) or alkyl groups. However, the molecular origin of this preference is not yet understood. By a combination of methods including the activation strain model (ASM), energy decomposition analysis (EDA), molecular orbital (MO) theory, and conceptual density functional theory (CDFT), we disclosed the substituent effects of TADs. First, ASM/EDA analysis revealed that the reactivity of alkyl and aryl-substituted TADs is controlled by interaction energies, ΔE int, which are ultimately defined by orbital interactions between frontier molecular orbitals. Moreover, alkyl-TADs are also controlled by the extent of strain at the transition state. The MO analysis suggested that the rate acceleration for EWG-substituted TADs is due to a more favorable orbital interaction between the HOMO of anthracene and the LUMO of the TADs, which is corroborated by calculations of charge transfer at the transition states. From CDFT, the chemical potential of anthracene is higher than those of TADs, indicating a flow of electron density from anthracene to TADs, in agreement with the results from the electrophilicity index.

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Section: Introductionmentioning

confidence: 99%

Rationalizing the Substituent Effects in Diels–Alder Reactions of Triazolinediones with Anthracene

2022

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“…In recent years, click chemistry has become a promising strategy for designing nanogels due to its high reactivity, good selectivity, and mild reaction conditions. The thiol-ene click reaction is common in the addition of thiol to the double bonds under photo-initiation, which is efficient, high-yield, and can tolerate different functional groups (Tasdelen et al, 2016;Phan et al, 2020;Mondal et al, 2021). The PEG and polycyclic phenylborate nanogels loaded with insulin and glucose oxidase (Gox) were developed through a one-pot thiol-ene click chemistry method by using tetrathiol compound QT as a coupling agent (Li C. et al, 2019).…”

Section: Covalent Cross-linkingmentioning

confidence: 99%

Design and Applications of Tumor Microenvironment-Responsive Nanogels as Drug Carriers

Gao

Kang

et al. 2021

Front. Bioeng. Biotechnol.

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In recent years, the exploration of tumor microenvironment has provided a new approach for tumor treatment. More and more researches are devoted to designing tumor microenvironment-responsive nanogels loaded with therapeutic drugs. Compared with other drug carriers, nanogel has shown great potential in improving the effect of chemotherapy, which is attributed to its stable size, superior hydrophilicity, excellent biocompatibility, and responsiveness to specific environment. This review primarily summarizes the common preparation techniques of nanogels (such as free radical polymerization, covalent cross-linking, and physical self-assembly) and loading ways of drug in nanogels (including physical encapsulation and chemical coupling) as well as the controlled drug release behaviors. Furthermore, the difficulties and prospects of nanogels as drug carriers are also briefly described.

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“…Amino bisphosphonate copolymers were then synthesized by the click chemistry reaction of the preformed azido-functionalized copolyester with the alkyne-functionalized bisphosphonate developed. Click chemistry, widely used in the synthesis of many functionalized polymers, , guaranteed a high yield and purity of the synthesized products, required mild reaction conditions, and did not produce little byproducts . The interest of our synthetic pathway is that it allowed an easy introduction of bisphosphonate-based ligands, which are known to be quite difficult to prepare.…”

Section: Introductionmentioning

confidence: 99%

α-Aminobisphosphonate Copolymers Based on Poly(ε-caprolactone)s and Poly(ethylene glycol): A New Opportunity for Actinide Complexation

Arrambide,

Ferrie,

Prelot

et al. 2023

Biomacromolecules

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Original α-aminobisphosphonate-based copolymers were synthesized and successfully used for actinide complexation. For this purpose, poly(α-chloro-ε-caprolactone-co-ε-caprolactone)b-poly(ethylene glycol)-b-poly(α-chloro-ε-caprolactone-co-ε-caprolactone) copolymers were first prepared by ring-opening copolymerization of ε-caprolactone (εCL) and α-chloro-εcaprolactone using poly(ethylene glycol) (PEG) as a macroinitiator and tin(II) octanoate as a catalyst. The chloride functions were then converted to azide moieties by chemical modification, and finally α-aminobisphosphonate alkyne ligand (TzBP) was grafted using click chemistry, to afford well-defined poly-(αTzBPεCL-co-εCL)-b-PEG-b-poly(αTzBPεCL-co-εCL) copolymers. Three copolymers, showing different α-aminobisphosphonate group ratios, were prepared (7, 18, and 38%), namely, CP8, CP9, and CP10, respectively. They were characterized by 1 H and 31

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Macromolecular engineering in functional polymers via ‘click chemistry’ using triazolinedione derivatives

Cited by 28 publications

References 207 publications

Rationalizing the Substituent Effects in Diels–Alder Reactions of Triazolinediones with Anthracene

Rationalizing the Substituent Effects in Diels–Alder Reactions of Triazolinediones with Anthracene

Design and Applications of Tumor Microenvironment-Responsive Nanogels as Drug Carriers

α-Aminobisphosphonate Copolymers Based on Poly(ε-caprolactone)s and Poly(ethylene glycol): A New Opportunity for Actinide Complexation

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