Copper-Catalyzed vs Thermal Step Growth Polymerization of Starch-Derived α-Azide−ω-Alkyne Dianhydrohexitol Stereoisomers: To Click or Not To Click?

Besset, Céline; Binauld, Sandra; Ibert, Mathias; Fuertès, Patrick; Pascault, Jean‐Pierre; Fleury, Étienne; Bernard, Julien; Drockenmuller, Éric

doi:10.1021/ma9024784

Cited by 71 publications

(74 citation statements)

References 43 publications

(14 reference statements)

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“…PTs having a random sequence of 1,4and 1,5-disubstituted units) with broader solubility and T g , M n and Ð values comparable to their regioisomeric analogs could be readily prepared by TAAC polyaddition of α-azide-ω-alkyne monomers in bulk. 104 Therefore, the functional tolerance and robust nature of this straightforward thermally initiated bulk polyaddition allowed to envision a monotopic approach where chain extension and in-situ N-alkylation of the resulting mixture of 1,4-and 1,5-disubstituted 1,2,3-triazoles occur concomitantly. This approach has thus been applied to the preparation of TPILs 101-112 from α-azide-ω-alkyne monomers 71-74, showing that it could be applied to different N-3 groups (i.e.…”

Section: Tpils Obtained Via Taac: Development Of Monotopic Approachesmentioning

confidence: 99%

Poly(1,2,3-triazolium)s: a new class of functional polymer electrolytes

2016

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Poly(ionic liquid)s (PILs) are a unique class of polyelectrolytes having properties suited for modern technological applications such as electrochemical devices (batteries, supercapacitors, light-emitting electrochemical cells), ion-gated field effect transistors, electrochromic devices, fuel cells, dye sensitized solar cells, catalysis, or soft robotics. Their structure and properties can be finely tuned by unlimited combinations issued from extended pools of cationic and anionic building blocks. In a constant quest for the development of solid polymer electrolytes with enhanced physical, mechanical and (electro)chemical properties, a new class of PILs based on 1,2,3-triazolium cations has been recently developed. Their preparation takes advantage of the beneficial features of the multiple combinations between the Click chemistry philosophy with macromolecular engineering techniques to afford tunable and highly functional ion conducting materials thus stretching out the actual boundaries of PILs macromolecular design. This feature article summarizes the different strategies developed so far for the synthesis of 1,2,3-triazolium-based PILs (TPILs) since their first introduction in 2013.

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Section: Tpils Obtained Via Taac: Development Of Monotopic Approachesmentioning

confidence: 99%

Poly(1,2,3-triazolium)s: a new class of functional polymer electrolytes

2016

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“…[43] Free amines were obtained after hydrogenation of benzylamino derivatives or azides. [40b,c] Methylation was performed either via an Eschweiler-Clark reaction followed by quaternization [34] or via a phase-transfer catalyzed reaction in a biphasic medium with Me 2 SO 4 , to lead to mono ammonium or imidazolium derivatives.…”

Section: Preparation Of Diaminesmentioning

confidence: 99%

Nitrogen-functionalized Isohexides in Asymmetric Induction

Janvier

Moebs‐Sanchez

Popowycz

2016

Chimia

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“…Drockenmuller and coworkers have prepared these type of monomers by conversion of the two reactive alcohol groups of 1,4:3,6-dianhydrohexitols, such as isomannide, isosorbide and isoidide, into azide and/or alkyne functions. The polymerization of ␣-azide--alkyne monomers furnished the corresponding linear AB-polytriazoles [12,13], while the analogous A 2 B 2 polymers have been prepared by polymerization of diazide (AA) and dialkyne (BB) comonomers [13,14]. Partially biosourced networks were also obtained by reaction of one of the AB monomers with an A 2 B 2 aliphatic cross-linker [13,14].…”

Section: Introductionmentioning

confidence: 99%

“…Di-O-methylidene-N-(but-3-yn-1-yl)-6-O-tosyl-dgluconamide(12). A solution of compound 10 (0.138 g, 0.51 mmol) and tosyl chloride (0.152 g, 0.80 mmol) in pyridine (0.9 mL) was stirred at room temperature overnight.…”

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confidence: 99%