Preparation, cation-anion interactions and physicochemical properties of ether-functionalized imidazolium ionic liquids

Schrekker, Henri Stephan; Silva, Dagoberto O.; Gelesky, Marcos Alexandre; Stracke, Marcelo Paulo; Schrekker, Clarissa M. L.; Gonçalves, Ricardo Júnior de Assis Fernandes; Dupont, Jaı̈rton

doi:10.1590/s0103-50532008000300009

Cited by 85 publications

(84 citation statements)

References 18 publications

(31 reference statements)

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“…This should be due to the star-shaped topological structure of STIIL hinders PEG chains wrapping around the imidazolium ring, the nucleophilic attack of Cl  on the imidazolium ring would become easier and resulted in the forward of onset of chemical degradation. Similarly, several examples also demonstrated that incorporating short length PEG chains to quaternary cations led to worse thermal stability than those with one or no ether groups [65,66] . The second weight loss step, started at ~302 C, comprising a significant fraction of 77 wt%, could be assigned to chemical degradation of STIIL, and kept constant after 400 C.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of poly(ethylene glycol) functionalized star-shaped tricationic imidazolium based ionic liquid

Zhang

Yin

et al. 2014

Chin J Polym Sci

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We report on the preparation of a well-defined star-shaped tricationic ionic liquid possessing three arms of poly(ethylene glycol) functionalized imidazolium rings. Remarkable solubility was found in most of the organic solvents we used. Thermogravimetric analysis (TGA) exhibited excellent thermal stability and two distinct decomposition temperatures were attributed to two kinds of chemical degradation. Differential scanning calorimetry (DSC) was further employed to investigate the thermal phase transitions, that three different signals (T g , T c , and T m ) were shown upon the second heating process. Moreover, CH 2 Cl 2 solution of the ionic liquid expressed an excitation-wavelength dependent fluorescence response, leading to the facile modulation of photoluminescence behavior. This work represents an example of utilizing molecular design to construct novel ionic liquids and endow further potential to be used in the engineering materials.

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Section: Resultsmentioning

confidence: 99%

Synthesis of poly(ethylene glycol) functionalized star-shaped tricationic imidazolium based ionic liquid

Zhang

Yin

et al. 2014

Chin J Polym Sci

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“…18 In the case of imidazolium ionic liquids, the stabilization of gold nanoparticles was found to be associated with the disclosure of the imidazolium cation. 19 Inverse micelles have been used to generate nanoparticles exhibiting appreciable degree of size and shape control 17,20 by providing effective nanoreactors with narrow size dispersion. On the other hand, these species can adsorb preferentially on some crystalline faces, promoting a faster growth of the less protected faces, leading to anisotropic particles such as nanorods.…”

Section: Preparation Of Gold Nanoparticlesmentioning

confidence: 99%

The coordination chemistry at gold nanoparticles

Toma¹,

Zamarion²,

Toma³

et al. 2010

J. Braz. Chem. Soc.

114

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Nas nanopartículas de ouro, as propriedades químicas e físicas são ditadas principalmente pelos átomos da superfície, os quais podem interagir com espécies doadoras-aceitadoras, ou ligantes, da mesma forma que os complexos metálicos correspondentes. Além disso, os elétrons podem entrar em ressonância com a luz incidente dando origem aos plasmons de superfície, que levam à intensificação do campo elétrico local e ao efeito SERS, proporcionando uma ampla variedade de aplicações na química, biologia e nanotecnologia. Ligantes de ponte, multifuncionais, podem ser usados para intermediar a ligação de íons metálicos aos átomos de ouro da superfície. Essa estratégia permite controlar a estabilização em solução através das cargas dos complexos metálicos, acrescentando, ao mesmo tempo, novas características químicas e maior funcionalidade às nanopartículas modificadas. Dessa forma, uma nova química de coordenação pode ser vislumbrada, combinando nanopartículas metálicas, como as de ouro, e complexos, à luz da química supramolecular e dos efeitos de ressonância plasmônica de superfície.In gold nanoparticles the surface metal atoms play a major role, determining their chemical and physical properties by interacting with donor-acceptor species or ligands in a similar way as the related metal complexes. In addition, coherent oscillations of the metal electrons in resonance with the frequency of the exciting light give rise to localized surface plasmons responsible for an enhancement of the local electric field and SERS effect, allowing a wide range of applications in chemistry, biology and nanotechnology. Multifunctional bridging ligands can be employed for simultaneously binding metal ions and surface atoms. The attractive point of this approach is the possibility of exploiting the charge controlled stabilization by the metal complexes, while imparting new characteristics and properties to the modified nanoparticles. As a matter of fact, a new, exciting field of coordination chemistry can be envisaged, combining metal nanoparticles and metal complexes, in the light of supramolecular and surface plasmon resonance effects.

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“…2 Besides ionic interactions, whether supramolecular interactions also govern the organization of imidazoliumbased ILs is still hotly debated with a vast number of important contributions. [24][25][26][27][28][29] Despite their importance, the number of significant contributions specifically discussing the supramolecular organization and interactions of TSILs is much scarcer [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] when compared to nonfunctionalized ILs. TSILs have become one of the most important strategies for furthering IL chemistry, 1 as noted for the large and increasing number of innovative applications described for these ionic compounds.…”

Section: Introductionmentioning

confidence: 99%

Solid, Solution and Gas Phase Interactions of an Imidazolium-Based Task-Specific Ionic Liquid Derived from Natural Kojic Acid

Neto¹,

Mota²,

Gatto³

et al. 2014

Journal of the Brazilian Chemical Society

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Um líquido iônico imidazólio de função específica derivado do ácido kójico natural teve suas interações supramoleculares investigadas no estado sólido, em solução e em fase gasosa. Diferentes técnicas como difração de raios X de monocristal, espectroscopia de ressonância magnética nuclear (NMR), espectrofotometria UV-Vis, medidas de condutividade, espalhamento de raios X em baixo ângulo (SAXS), espectrometria de massas (tandem) com ionização por electrospray (ESI-MS(/MS)) e cálculos teóricos permitiram uma investigação estrutural aprofundada desse líquido iônico de função específica e suas interações supramoleculares. An imidazolium-based task-specific ionic liquid derived from the natural kojic acid had its supramolecular interactions investigated in solid, solution and gas phase. The use of a set of techniques formed by single-crystal X-ray diffraction, nuclear magnetic resonance (NMR) spectroscopy, UV-Vis spectrophotometry, conductivity measurements, small angle X-ray scattering (SAXS), electrospray (tandem) mass spectrometry (ESI-MS(/MS)), and theoretical calculations allowed a deep investigation of the structural organization of the task-specific ionic liquid and its supramolecular interactions.Keywords: ionic liquids, imidazolium, task-specific ionic liquids, supramolecular interactions, organization, X-ray, SAXS, UV-Vis, NMR, ESI-MS IntroductionIonic liquids (ILs) and task-specific ionic liquids (TSILs), especially those based on the imidazolium cation, are part of a class of attractive compounds of widespread use in many scientific and technological areas.1-3 These organic salts have already been successfully used in the chemical industry for many years. 4 Their prominence is exemplified by many review articles recently published regarding several features of these unique chemical species. 5-21The possibility of tuning the physical and chemical properties of ILs and TSILs associated with their attractive physicochemical properties, such as very low vapor pressure, large electrochemical window, good thermal and chemical stabilities, have also opened a wealth of other applications for these ionic materials. Despite all progress already reached by ILs, fine details about their supramolecular organization, the importance of H-bonds and a deep understanding on the directionality of imidazolium-based derivatives are only now emerging. Each IL/TSIL has unique physicochemical properties and it has been estimated that ca. 10 6 combinations of known Neto et al. 2281 Vol. 25, No. 12, 2014 cations and anions may afford a new type of such ionic compounds. 22 The effort towards a better comprehension on the physicochemical properties of such materials is therefore very challenging; and each new structure demands specific efforts and a set of characterizations to depict its unique structural features and properties. Despite the diversity, some general trends have been established, and it is, for instance, known that the physicochemical properties of ILs/TSILs are intimately associated with their ionic structures, 23...

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Preparation, cation-anion interactions and physicochemical properties of ether-functionalized imidazolium ionic liquids

Cited by 85 publications

References 18 publications

Synthesis of poly(ethylene glycol) functionalized star-shaped tricationic imidazolium based ionic liquid

Synthesis of poly(ethylene glycol) functionalized star-shaped tricationic imidazolium based ionic liquid

The coordination chemistry at gold nanoparticles

Solid, Solution and Gas Phase Interactions of an Imidazolium-Based Task-Specific Ionic Liquid Derived from Natural Kojic Acid

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