Supramolecular liquid crystals of amide functionalized imidazolium saltsElectronic supplementary information (ESI) available: IR, proton and carbon NMR data for all compounds. See http://www.rsc.org/suppdata/jm/b2/b210562d/

Abstract

Liquid crystalline 1-acetamido-3-alkylimidazolium bromide, hexafluorophosphate and tetrafluoroborate salts with 3-alkyl chains of carbon number n ~10, 12, 14, 16 and 18 were prepared. The single crystal structure of the PF 6 2 salt of n ~12 self-organizes to form a framework of a hydrogen bonded ribbon polymer. The mesomorphic behaviors of these compounds were studied by polarized optical microscopy, differential scanning calorimetry and powder X-ray diffraction. The presence of extended hydrogen bonding interactions in these acetamidoimidazolium salts allows them to have a wide temperature range of the mesophase. Anions have a profound effect on the phase transition temperature, suggesting that both ionic and hydrogen bonding interactions play dominant roles in the mesomorphic behavior of these liquid crystalline compounds. {Electronic supplementary information (ESI) available: IR, proton and carbon NMR data for all compounds. See http://www.rsc.org/ suppdata/jm/b2/b210562d/ Scheme 1 Schematic representation of [C n , amide-im]X.Scheme 2 Hydrogen bonding motifs in primary amides.

Fabrication of Biocompatible, Luminescent Supramolecular Structures and Their Applications in the Detection of Dopamine

“…The synthetic method of [C 12 ImCONH 2 ]Br is similar with that of [N-C 12 , N′-COOH-Im]Br reported previously, − and the detailed steps are as follows: Imidazole (0.15 mol), acrylonitrile (0.24 mol), and methanol (16 mL) were added into a flask. The mixture was stirred at 55 °C for 8 h. The resultant solution was evaporated to remove the residual methanol and acrylonitrile. The product of the first step was mixed with 0.12 mol bromododecane and 20 mL of isopropyl alcohol under stirring for 24 h at 60 °C. The resultant solution was mixed with 60 mL of NaOH solution (m/m: 15%) and 35 mL of chloroform.…”

Crystal structure of 1-butyl-3-{2-[(indan-5-yl)amino]-2-oxoethyl}-1H-imidazol-3-ium chloride

“…Only the C-C bond between methylene atom C11 and the carbonyl carbon C10 is relatively short [C10-C11 = 1.506 (6) Å ] and thereby close to the shortest such bond reported to date, i.e. 1.502 Å for a related compound with no substituent on the amide and a dodecyl chain on the other side of the imidazolium cation (Lee et al, 2003a). In general, all bond lengths of the two moieties and the methylene linker are in rather close ranges with the largest differences observed being those which lead to further substituents.…”

Fluorocarbon and Hydrocarbon N‐Heterocyclic (C5–C7) Imidazole‐Based Liquid Crystals

“…[4] Imidazolium salts have been intensively investigated as ionic liquids and also introduced into ILC systems. [5][6][7][8][9][10] This is because the imidazolium unit is an excellent platform that can be designed to promote liquid-crystalline phases and is easily doped by a large diversity of anions. [11] Imidazolium-based ILCs including symmetrical and unsymmetrical molecular frameworks have been generated and most of them show smectic phases.…”