2021
DOI: 10.1002/anie.202106230
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Dynamic Nucleophilic Aromatic Substitution of Tetrazines

Abstract: A dynamic nucleophilic aromatic substitution of tetrazines (SNTz) is presented herein. It combines all the advantages of dynamic covalent chemistry with the versatility of the tetrazine moiety. Indeed, libraries of compounds or sophisticated molecular structures can be easily obtained, which are susceptible to post‐functionalization by inverse electron demand Diels–Alder (IEDDA) reaction, which also locks the exchange. Additionally, the structures obtained can be disassembled upon the application of the right … Show more

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Cited by 47 publications
(51 citation statements)
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References 146 publications
(169 reference statements)
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“…Unfortunately, such recyclable polymers often lack the required thermal stability, and monomer recovery is usually a costly process. In this regard, dynamic covalent polymers have arisen as an efficient and inexpensive way to garner recyclable polymers. As has been shown above, polymer networks made by S N Tz show a good thermal stability, but even more interesting, alkyl thiols have a clear tendency to displace phenols from the tetrazine ring . Such an ability can be used to completely degrade the polymers with a thiol in the presence of triethylamine as a base to promote the reaction.…”
Section: Resultsmentioning
confidence: 99%
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“…Unfortunately, such recyclable polymers often lack the required thermal stability, and monomer recovery is usually a costly process. In this regard, dynamic covalent polymers have arisen as an efficient and inexpensive way to garner recyclable polymers. As has been shown above, polymer networks made by S N Tz show a good thermal stability, but even more interesting, alkyl thiols have a clear tendency to displace phenols from the tetrazine ring . Such an ability can be used to completely degrade the polymers with a thiol in the presence of triethylamine as a base to promote the reaction.…”
Section: Resultsmentioning
confidence: 99%
“…Indeed, the traditional way to modulate the properties of polymer structures is making different polymers from modified monomers. However, postfunctionalization is so attractive because it allows one to easily modulate the properties of a single material by just attaching different fragments to the backbone. , In our case, cis -5-norbornene- endo -2,3-dicarboxylic acid ( 6 ) was chosen as a reactive olefin for the IEDDA reaction, mainly because it displays two polar groups that can modify the properties of the polymer after the functionalization. Heating a suspension of P1 and 6 in acetonitrile at 80 °C for 72 h yielded P1 DA as a brownish solid in 70% yield.…”
Section: Resultsmentioning
confidence: 99%
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“…Column chromatography was carried out using silica gel 60 (230-400 mesh ASTM). 1 H NMR spectra were recorded at 500 MHz and 400MHz, 13 C NMR spectra were recorded at 126 MHz and 100 MHz. Solid state 13 C NMR were recorded with a VARIAN INOVA-750.…”
Section: Methodsmentioning
confidence: 99%