The Effect of the Cation π‐Surface Area on the 3D Organization and Catalytic Ability of Imidazolium‐Based Ionic Liquids

D’Anna, Francesca; Marullo, Salvatore; Vitale, Paola; Noto, Renato

doi:10.1002/ejoc.201100763

Cited by 39 publications

(30 citation statements)

References 87 publications

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“…Imidazolium‐based DOSs 19 (Scheme , R = C 4 H 9 ) based on a xylene unit as spacer and [NTf 2 – ] as the anion have been used by us as reaction media to study the thermally induced rearrangement of heterocycles, such as the ( Z )‐phenylhydrazone of 3‐benzoyl‐5‐phenyl‐1,2,4‐oxadiazole into the corresponding triazole at 90 °C (Scheme ) 38. This reaction occurs through a highly ordered cyclic quasi‐aromatic transition state.…”

Section: Applicationsmentioning

confidence: 99%

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

D’Anna¹,

Noto²

2014

Eur J Org Chem

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During recent years growing interest has been devoted to the synthesis and applications of polycationic organic salts. Among them, di‐ and tricationic organic salts can be considered the natural evolution of monocationic ones. These last have given rise to the large class of ionic liquids. In the cases of di‐ and tricationic organic salts, the potential to change their structural features simply by varying the properties either of the charged heads or of the spacers separating them provides the opportunity to obtain materials suitable for different applications. This review article highlights recent progress in the study of the properties of di‐ and tricationic organic salts, as well as in some of their uses as solvent systems, receptors for anion recognition, ionic liquid crystals, low‐molecular‐weight gelators, additives for dye‐sensitized solar cells, and so on.

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Section: Applicationsmentioning

confidence: 99%

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

D’Anna¹,

Noto²

2014

Eur J Org Chem

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“…As probe reaction, it could be of a certain interest as, otherwise the MHR reaction, this is a bimolecular reaction and could allow shedding light on different factors affecting catalytic ability of the used TSDILs. [28][29][30] This base catalysed reaction is of great significance as it represents a useful synthetic strategy for the obtainment of intermediate nitriles able to give 4-oxobutanamides, which are found in a lot of natural and unnatural compounds displaying both pharmacological and biological properties.…”

Section: Introductionmentioning

confidence: 99%

Functionalised diimidazolium salts: the anion effect on the catalytic ability

2016

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aThe catalytic ability of some functionalised diimidazolium ionic liquids was tested using the Michael addition of malononitrile to t-chalcone as probe reaction. Diimidazolium salts characterized by the presence of 1-(1imidazolylmethyl)-3,5-di-[1-(3-octylimidazolylmethyl)]benzene cation and differing in the anion structure were used. Both mono-and dianions were employed and among these some chiral anions generally used as organocatalysts were taken into account. Data collected were analysed both as function of ionic liquids structure and basicity, evaluated using the Hammett basicity function. Although the use of chiral anions did not allow performing a stereochemical control of the reaction, data collected demonstrate the high catalytic ability of the functionalised salts. Indeed, high conversions and yields were obtained under mild conditions and in significantly shorter reaction times with respect to the ones so far reported for this reaction.

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“…[17] Notably,t he nature of the spacer interposed between the charged heads can introduce af urtherd egree of control on their behavior. In this context, in the last years we have studied the properties of dicationic imidazolium salts bearing as ymmetrically substituted aromatic spacer.B yi ntroducing subtle structural changes,s uch as by varying the alkyl chain length, the nature of the anion, andt he substitution pattern of the spacer, we have been able to obtain more organized reaction media, [18] selectiveh osts for anion recognition, [19] and low molecular weight gelators. [20] Moreover,c ombining p stacking with the highly directional nature of hydrogen bonds may serve as af urther tool to tune the spatiala rrangement of the monomersc onstituting the aggregates.…”

Section: Introductionmentioning

confidence: 99%

Aggregation Processes of Perylene Bisimide Diimidazolium Salts

D’Anna

Marullo

Lazzara

et al. 2015

Chemistry A European J

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The supramolecular aggregation of three diimidazolium-functionalized perylene bisimides, differing in the alkyl chain length was investigated. These salts form aggregates in solvents like chloroform, dichloromethane, and glycerol. Solvent-, concentration-, and temperature-dependent spectroscopic studies were carried out, evidencing the occurrence of an isodesmic, enthalpy-driven aggregation process, underpinned by π-π stacking and hydrogen bonding. Moreover, dynamic light scattering (DLS) measurements and SEM images revealed that these salts aggregate in chloroform into elongated structures.

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The Effect of the Cation π‐Surface Area on the 3D Organization and Catalytic Ability of Imidazolium‐Based Ionic Liquids

Cited by 39 publications

References 87 publications

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

Di‐ and Tricationic Organic Salts: An Overview of Their Properties and Applications

Functionalised diimidazolium salts: the anion effect on the catalytic ability

Aggregation Processes of Perylene Bisimide Diimidazolium Salts

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