High-throughput approach for the identification of anilinium-based ionic liquids that are suitable for electropolymerisation

Abstract

We report the synthesis of new protic ionic liquids (PILs) based on aniline derivatives and the use of high-throughput (HT) techniques to screen possible candidates. In this work, a simple HT method was applied to rapidly screen different aniline derivatives against different acids in order to identify possible combinations that produce PILs. This was followed by repeating the HT process with a Chemspeed robotic synthesis platform for more accurate results. One of the successful combinations were then chosen to be synthesised on a larger scale for further analysis. The new PILs are of interest to the fields of ionic liquids, energy storage and especially, conducting polymers as they serve as solvents, electrolytes and monomers at the same time for possible electropolymerisation (i.e. a self-contained polymer precursor).

The effect of alkyl chain and electronegative atoms in anion on biological activity of anilinium carboxylate bioactive ionic liquids and computational approaches by DFT functional and molecular docking

“…However, the absence of –COOH and –NH 2 group indicated the conversion of amine and carboxylate groups in ammonium carboxylate ILs. In case of FTIR, the strong peaks at about 3429 cm −1 (N–H) asymmetry and 3004 cm −1 (N–H) symmetry provide the presence of ammonium ion [ 61 ], as well as the another two peaks at 1780 cm −1 (C–O) asymmetry, 1675 cm −1 (-CO) symmetry confirm the existence of carboxylate ion [ 62 ]. However, the almost similar FTIR peaks were obtained for IL01, IL02, IL03 and IL04.…”

Trialkylammonium salt degradation: implications for methylation and cross-coupling

“…74 As such, the implications of the above results on a broader range of chemistries involving trimethylanilinium salts is also worth delineating. In our estimation, the fundamental understanding of the structural parameters affecting anilinium salt degradation hold implications for: (i) the design of anilinium-derived ionic liquids used as solvents, electrolytes, and in electropolymerisation strategies, 75,76 (ii) the design and understanding of anilinium-derived compounds used in antibacterial technologies, 77,78 (iii) understanding the reaction conditions and range of anilinium substitution patterns amenable to metal-catalysed chemistries (including but not limited to arylation, alkynylation, silylation, and ortho-methylation), 7,8,23,29,31,79 (iv) understanding substrate design for 18 F radiolabelling mediated by S N Ar chemistries on anilinium cores, 12,80 and (v) a fuller understanding of the range of anilinium structures applicable to ion-pair directed regiocontrol of C-H activation methods. Fig.…”

Automated robotic platforms in design and development of formulations

“…63 Systems for carrying out reactions in parallel under different conditions have been implemented by Chemspeed, Hel Ltd., and other vendors. [64][65][66][67][68][69][70][71][72][73][74][75][76][77][78][79][80][81] Specifically, high-and medium-throughput facilities have been implemented in the pharmaceutical industry, where large numbers of compounds and reactions should be screened. Some examples are represented by high-capacity storage facilities handled by moving robots and/or robotic arms and miniaturized prototypes for synthesis and testing.…”

“…Systems for carrying out reactions in parallel under different conditions have been implemented by Chemspeed, Hel Ltd., and other vendors 64‐81 . Specifically, high‐ and medium‐throughput facilities have been implemented in the pharmaceutical industry, where large numbers of compounds and reactions should be screened.…”