Part 2: Poly(isobutylene)-based ionic liquids (PIBILs)
N, N-Triethylammonium telechelic PIB bis(trifluoromethylsulfonyl)imide (15c)
Red brown, highly viscous liquid, yield of 15c: 98% (196 mg). Mn= 8321 g/mol, Mw/Mn= 1.4, 1H NMR (400 MHz, CDCl3, δ ppm): 8.66 (s, 1H), 7.22 (d, J= 8.7 Hz, 2H), 6.79 (d, J= 8.8 Hz, 2H) 4.76 (m, 4H), 4.64 (t, J= 7.1 Hz, 2H), 3.98 (t, J= 5.7 Hz, 2H), 3.32 (q, J= 7.2 Hz, 6H), 2.40 (m, 2H) 1.29 (t, J= 2.5 Hz, 9H), 1.95−1.05 (m, 878H), 1.04-0.99 (s, 15H), 0.98−0.79 (m,107 H). 13C NMR (100, MHz, CDCl3, δ ppm):
156.1, 143.1, 136.6, 135.1, 128.7, 127.1, 113.7, 64.3, 59.5, 58.2, 53.4, 32.4, 7.8. 19F NMR (400 MHz, CDCl3, δ ppm): -78.81.
102 4. Summary
The aim of this work was to develop an efficient synthetic approach toward polymeric ionic liquids (POILs) and investigate the properties of the obtained materials with regard to the nature of the polymer, chain length, and the type of the associating cations and anions. In this respect, two different polymers, poly(ethylene glycol) and poly(isobutylene), with different molecular weights were selected as hydrophilic and hydrophobic polymers to be transformed to imidazolium, pyrrolidinium, and ammonium based polymeric ionic liquids.
Poly(ethylene glycol)-based ionic liquids (PEGILs)
Figure 4.1. Schematic representation of different strategies toward synthesis of TEGILs, HEXILs, and PEGILs.
Poly(ethylene glycol)s with n=3 (TEG), 5 (HEX), 8, and 33 (PEG) were planned to react with the corresponding amines to obtain the poly(ethylene glycol)-based ionic liquids. Tetraethylene glycol (n=3) was selected as a model structure to evaluate the condition of the quaternization reaction for the synthesis of the poly(ethylene glycol)-based ionic liquids. As the chain length was short, the reaction succeeded smoothly and resulted in 1a,b, 2a,b with a reasonable yield. Further variation in the structure of the synthesized ionic liquids (3a,b) was achieved via anion exchange. With increasing
103 the polymer chain length, efficient synthesis of the projected PEGILs (4a,b and 5a) became difficult due to incomplete conversion of the functional groups of the primary polymer chain. Thus, azide/alkyne “click” reaction was developed as a new strategy to attach the ionic moieties to the body of the polymer chain. For this reason, azido- derivative of hexaethylene glycol (n=5) was conducted with alkyne compounds bearing desired ionic moiety (24, 25c). The reaction of the azido- functionalized hexaethylene glycol with corresponding alkyne moieties in the presence of Cu (I) catalyst and microwave or conventional heating resulted in efficient synthesis of the projected products (6a-c, 7a-c). A similar procedure was extended to poly(ethylene glycol)s with longer chain length (n=8, 33), where the quaternization reaction failed. Accordingly, azide/alkyne “click” reaction resulted in successful synthesis of poly(ethylene glycol)-based ionic liquids with different chain length as well as different cations and anions (8,9b and 10a,b). The profound characterization of the all synthesized compounds was performed via spectroscopic methods. 1H and 13C NMR provided firm evidence of the existence and purity of the materials. Furthermore, ESI-TOF-MS analysis of the synthesized materials verified the presence of the projected structures for both oligomeric and polymeric ionic liquids. It is worth to mention that, ESI-TOF-MS analysis of the oligomeric ionic liquids revealed the formation of the variety of aggregates from ionic liquids associated with corresponding counter anions, Br-, Cl-, or combinations of two anions. TGA and DSC analysis also provided valuable information about thermal behavior of the synthesized materials. According to the results, all synthesized materials exhibited higher thermal stability (293-431 °C) comparing to their analogous oligomers or polymers without ionic moieties. Increasing chain length resulted in decreasing thermal stability. Pyrrolidinium derivatives demonstrated higher thermal stability comparing to imidazolium and ammonium where the anions and the chain length were identical. The influence of the associating anion on thermal stability of the synthesized ionic liquids determined as follow: Tf2N
->MsO->Cl-.
Poly(isobutylene)-based ionic liquids (PIBILs)
To investigate the influence of the ionic moieties on physical and mechanical properties of a hydrophobic polymer, a series of novel poly(isobutylene)-based ionic liquids were successfully synthesized (11-13a,b,c). The designed PIBILs were consisted of polymers with two different molecular weights (~8000 and ~3000 g.mol-1). First, isobutylene was polymerized via living carbocationic polymerization (LCCP) and quenched with two different quenching agents which
104 results in alkene and bromo functionalized telechelic polymers. These polymers were converted to azido functionalized PIB (27, 29 and 30) and were reacted with imidazolium, pyrrolidinium, and ammonium derivatives bearing alkyne moieties (26a-c). The azide/alkyne “click” reaction was performed under microwave irradiation, in the presence of CuI as a catalyst. Further variation in anion combination was achieved via anion exchange in the solution of lithium bistriflimide salt (14-15a,b,c).
Figure 4.2. Schematic representation of different strategies toward synthesis of PIBILs.
All of the synthesized POILs were characterized by 1H and 13C NMR spectroscopy. 19F NMR and IR spectroscopy were used to confirm the occurrence of the anion exchanges. Furthermore, the structure of the synthesized polymers was also proved by MALDI-TOF analysis. TGA analysis of the synthesized POILs demonstrated two decomposition points for most of the products. The first decomposition was detected in the range of 100-210 °C and attributed to the moisture and solvent residue trapped in the product, while the main decomposition occurred around 367–395 °C. Both cation and anion had influence on the thermal stability of the synthesized products. For the first series of the products the cation effect was significant as the anions were identical. However, for the second series of the materials the effect of the anion was more pronounced. In general, POILs containing bromide exhibited a higher thermal stability in comparison to bistriflimide counter anion.
105 Meanwhile, DSC analysis proved a slight increase in Tg of the products as a result of the presence of the ionic moieties. Furthermore, all synthesized PIBILs associated with bistriflimide anion exhibited an additional Tg as a result of the formation of the clusters according to EHM theory. Due to high polarity difference between ionic end group and hydrophobic nature of poly(isobutylene), the synthesized POILs constructed multiplets with restricted mobility regions resulted in cluster formation, similar to the behavior of ionomers. The occurrence of such phenomenon in all synthesized PIBILs except 15a-c is proved by means of SAXS measurements. According to the results, the confirmed nanostructural organizations were detected in simple cubic confinement at room temperature. Furthermore, temperature dependent in situ SAXS measurements of the samples demonstrated a reversible temperature dependent order-disorder transition, in most of the synthesized PIBILs. The short relaxation time required for the restoration of the primary ordered structure was implying the self healing ability of the designed materials. Rheological measurements on the synthesized PIBILs confirmed the existence of the nanostructural organizations. According to the results, the constructed multiplets in the cluster were sliding on each other resulting in a rubbery plateau up to the temperature where the cluster was destroyed.
Figure 4.3. Schematic representation of the formation of multiplet and cluster resulted in ordered structure with simple cubic confinement. Increasing the temperature leads to the reversible destruction of the clusters and flow of the material as an indication of self healing behaviour.
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