Triazolium cations: from the “click” pool to multipurpose applications

Aizpurua, J. M.; Fratila, Raluca M.; Monasterio, Zaira; Pérez-Esnaola, Nerea; Andreieff, Elena; Irastorza, Aitziber; Sagartzazu‐Aizpurua, Maialen

doi:10.1039/c3nj00667k

Cited by 121 publications

(58 citation statements)

References 57 publications

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“…41,42 The synthesis of TILs generally involves the initial preparation of 1,4-dialkyl-1,2,3triazoles, followed by the N-alkylation of the N-3 position and optional anion exchange reaction (Fig. 5).…”

Section: Synthesis and Application Of 123-triazoliumsmentioning

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: Synthesis and Application Of 123-triazoliumsmentioning

confidence: 99%

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

2016

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“…However, native starch can not meet the demands for further industrial applications on account of lacking active groups 2014; Zhang, Wei, Vijaya Kumar, Rasheed, & Zhou, 2014), anticancer (Kumar et al, 2011), antimalarial (Pereira et al, 2014), and antioxidant (Tan, Li, Li, Dong & Guo, 2016), have also facilitated the chemical modification of polysaccharide with 1,2,3-triazoles. Meanwhile, alkylation of 1,2,3-triazoles can provide the 1,2,3-triazolium cations, which have been prepared for novel ionic liquids (Mudraboyina, Obadia, Abdelhedi-Miladi, Allaoua, & Drockenmuller, 2015;Obadia, Crépet, Serghei, Montarnal, & Drockenmuller, 2015;Obadia et al, 2014) and catalysts (Aizpurua et al, 2014;Jha & Jain, 2013;Ohmatsu, Hamajima, & Ooi, 2012) because of high thermal stability, tunable solubility, and low flammability . However, although the 1,2,3-triazole-linked starch derivatives have been reported and described, to our knowledge there are no reports on synthesis and bioactivity of starch derivatives bearing 1,2,3-triazolium cations so far.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis of novel starch derivative bearing 1,2,3-triazolium and pyridinium and evaluation of its antifungal activity

Tan

Gao

et al. 2017

Carbohydrate Polymers

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“…However, recently 1,2,3-triazolium ionic liquids are gaining popularity as phase tags, catalysts and solvents [8,9,23,24]. Here, we provide a comprehensive up-to-date review on the synthesis, properties and applications of 1,2,3-triazolium ILs.…”

Section: Introductionmentioning

confidence: 99%

Chemistry of 1,2,3-Triazolium Salts

Yacob¹,

Liebscher²

2014

Topics in Heterocyclic Chemistry

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1,2,3-Triazolium salts have been known for a long time. However, their potential as ionic liquids and catalysts was recognized only quite recently. 1,2,3-Triazolium ionic liquids can serve as solvent, as catalyst, as hosts in anion recognition and as components of molecular machines. The major trends in application involve tethering catalytically active species such as (S)-proline with triazolium ionic liquids and the use as anion recognizing organocatalysts. Such catalysts are interesting not only due to their recyclability but also because of their outstanding tuneable properties. They can have wide liquid range, thermal stability, tuneable polarity, low flammability, tuneable solubility and low vapour pressure along with ease of separation. The syntheses of 1,2,3-triazolium salts are mainly based on the copper catalysed azide-alkyne cycloaddition (CuAAC) as the most famous click reaction, and subsequent N-alkylation of the resulting 1,2,3-triazoles. This synthetic route has the advantage of having four structural units, i.e. the alkyne, the azide, the alkylating agent and the counter anion that can be manipulated in order to tune the properties of the resulting ionic liquid. Unlike the imidazolium ionic liquids 1,2,3-triazolium salts do not have an acidic proton at position 2, which could make them inappropriate for reactions under basic conditions. The low acidity of 1,2,3triazolium salts in position 4 is exploited in the formation of 1,2,3-triazol-4-ylidene metal complexes with marked catalytic properties.

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Triazolium cations: from the “click” pool to multipurpose applications

Cited by 121 publications

References 57 publications

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

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

Design, synthesis of novel starch derivative bearing 1,2,3-triazolium and pyridinium and evaluation of its antifungal activity

Chemistry of 1,2,3-Triazolium Salts

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