Valorization of Plastic Wastes for the Synthesis of Imidazolium‐Based Self‐Supported Elastomeric Ionenes

Abstract

Imidazolium‐based ionenes are known to be high‐performance materials for a great variety of applications. The preparation of these polymers requires the use of bis‐imidazole starting monomers, which are commonly prepared by using toxic chloride reagents. In this study, bis‐imidazole monomers are synthesized by organocatalytic chemical recycling of discarded plastics through chemical depolymerization. By using poly(ethylene terephthalate) and bisphenol A polycarbonate as starting materials, different monomers containing amide or urea functionalities are prepared to produce high‐molecular‐weight ionic polymers. These novel ionenes show excellent elastomeric and self‐healing behavior, serving as a promising means to expand the exploration of plastic wastes as a source of new materials.

Designing Imidazolium Poly(amide-amide) and Poly(amide-imide) Ionenes and Their Interactions with Mono- and Tris(imidazolium) Ionic Liquids

“…There have been abundant research efforts in recent decades dedicated to the design and applications surrounding polyelectrolytes and ionomers which contain charged features pendant to the main chain, highlighted in several reviews [1][2][3][4][5][6]. The design of ionic liquids (ILs) undoubtably serves as an influential synthetic inspiration for polyelectrolytes, which possess essentially The utility of ionenes has been demonstrated in separations and CO2 capture [8][9][10][11][12][13], ionexchange or conducting membranes [14], antimicrobial coatings [15][16][17][18], batteries [19][20][21], electrochromic devices [22], hydrogels and gelators [23][24][25], water treatment [26], and fiber applications [12,27,28]. Nearly all known ionenes bear cationic moieties such as ammonium, phosphonium, pyrrolidinium, pyridinium, triazolium, and imidazolium groups [8,14,20,22,23,[29][30][31][32][33][34].…”

“…Only a few examples of polyamide (PA) ionenes have been demonstrated in literature, typically containing ammonium, pyridinium, and imidazolium cations. Our group has introduced aliphatic and aromatic imidazolium-based PA ionenes used as gas separation membranes or self-healing elastomers [10,12,27,28]. We have also recently demonstrated that some of the key monomers for these PA ionenes can be derived from poly(ethylene terephthalate) (PET).…”

“…These methods allow for the controlled sequencing and spacing of functionality using only two monomers, with distributed ionic groups located between these features. In our previous work, we have introduced multiple series of PA and PI ionenes, and reported that these ionene systems undergo ordering when "free" imidazolium IL is present [9][10][11][12]27,28,36]. This free IL serves as a non-covalent crosslink between ionene chains.…”

“…The utility of ionenes has been demonstrated in separations and CO 2 capture [ 8 , 9 , 10 , 11 , 12 , 13 ], ion-exchange or conducting membranes [ 14 ], antimicrobial coatings [ 15 , 16 , 17 , 18 ], batteries [ 19 , 20 , 21 ], electrochromic devices [ 22 ], hydrogels and gelators [ 23 , 24 , 25 ], water treatment [ 26 ], and fiber applications [ 12 , 27 , 28 ]. Nearly all known ionenes bear cationic moieties such as ammonium, phosphonium, pyrrolidinium, pyridinium, triazolium, and imidazolium groups [ 8 , 14 , 20 , 22 , 23 , 29 , 30 , 31 , 32 , 33 , 34 ].…”

“…Previous literature by Bara and coworkers has demonstrated the expansive possibilities of imidazolium ionenes, shifting toward more “high-performance” materials and exploring the effects of introducing imidazolium ILs into the ionene matrix [ 9 , 10 , 13 , 28 , 36 , 40 , 41 ]. We have demonstrated the suitability of imidazolium ionenes applied as CO 2 -selective gas separation membranes, self-healing and shape memory materials, 3D printing feedstocks, and as fibers [ 9 , 10 , 11 , 12 , 13 , 27 , 28 ]. The tailorability of this imidazolium platform is vast, when creative chemistries are employed to probe the effects of structural or connective variation of the cyclic cation, substitution, charge density, functionality, and modification of properties via addition of ILs.…”