Sulfur makes the difference: synthesis and mesomorphic properties of novel thioether-functionalized imidazolium ionic liquid crystals

Mansueto, Markus; Kreß, Katharina Christina

doi:10.1016/j.tet.2014.03.050

Cited by 10 publications

(6 citation statements)

References 60 publications

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“…568 The influence of a sulfur atom in the side chain of 1-methyl-3-(n-alkyl)imidazolium salts was studied by Laschat and coworkers (29-X-n). 619 Sulfur atoms have a "softer" character than oxygen and nitrogen atoms, due to their more delocalized dorbitals. In the case of the triflate salts, the presence of a sulfur atom appears to have a beneficial effect on the LC properties in the sense that compounds 29-OTf-n show lower melting points and larger mesophase widths than the related [C n mim][OTf] salts.…”

Section: Imidazolium-based Mesogens Having a Predominantly Amphiphili...mentioning

confidence: 99%

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Ionic Liquid Crystals: Versatile Materials

et al. 2016

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This Review covers the recent developments (2005-2015) in the design, synthesis, characterization, and application of thermotropic ionic liquid crystals. It was designed to give a comprehensive overview of the "state-of-the-art" in the field. The discussion is focused on low molar mass and dendrimeric thermotropic ionic mesogens, as well as selected metal-containing compounds (metallomesogens), but some references to polymeric and/or lyotropic ionic liquid crystals and particularly to ionic liquids will also be provided. Although zwitterionic and mesoionic mesogens are also treated to some extent, emphasis will be directed toward liquid-crystalline materials consisting of organic cations and organic/inorganic anions that are not covalently bound but interact via electrostatic and other noncovalent interactions.

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Section: Imidazolium-based Mesogens Having a Predominantly Amphiphili...mentioning

confidence: 99%

“…The influence of a sulfur atom in the side chain of 1-methyl-3-( n -alkyl)imidazolium salts was studied by Laschat and co-workers ( 29-X- n ) . Sulfur atoms have a “softer” character than oxygen and nitrogen atoms, due to their more delocalized d-orbitals.…”

Section: Imidazolium-based Ionic Liquid Crystalsmentioning

confidence: 99%

Ionic Liquid Crystals: Versatile Materials

et al. 2016

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“…Rich polymorphism was observed for asymmetrically end‐capped oligothiophenes upon attachment of thioethers [8] . Upon S/O replacement in the side chains of calamitic imidazolium ILCs, a pronounced decrease of the melting temperatures was detected, while clearing transitions remained constant or even increased, resulting in significantly broadened mesophase ranges [9] . For methylimidazolium ILCs the emergence of mesomorphic properties via the sulfur motif was reported [10] .…”

Section: Introductionmentioning

confidence: 98%

“…[8] Upon S/O replacement in the side chains of calamitic imidazolium ILCs, a pronounced decrease of the melting temperatures was detected, while clearing transitions remained constant or even increased, resulting in significantly broadened mesophase ranges. [9] For methylimidazolium ILCs the emergence of mesomorphic properties via the sulfur motif was reported. [10] Stabilization of mesophases was also found for columnar palladium complexes with dipicolinic acid-derived pincer ligands [11] and columnar crown ethers carrying thioethers instead of alkoxy side chains.…”

Section: Introductionmentioning

confidence: 99%

Chasing Self‐Assembly of Thioether‐Substituted Flavylium Salts in Solution and Bulk State

et al. 2022

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Dedicated to Professor Herbert Mayr on the occasion of his 75th birthdayTwo series of flavylium triflates carrying alkoxy side chains in the A-ring (benzo unit of chromylium salt) and thioethers in the B ring (phenyl unit) (O n -Fla-S m ) as well as thioethers at both A and B ring (S n -Fla-S m ) were synthesized in order to understand the effect of thioether functionalization on their self-assembly and electronic properties. Concentration-dependent and diffusion ordered (DOSY) NMR experiments of O 1 -iV-Fla-S 3 indicate the formation of columnar H-aggregates in solution with antiparallel intracolumnar stacking of the AC unit (chromylium) of the flavylium triflate, in agreement with the solid state structure of O 1 -V-Fla-S 1 . Thioether substitution on the B ring changes the linear optical properties in solution, whereas it has no effect on the A ring. According to differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction bulk self-assembly of these ionic liquid crystals (ILCs) depends on the total number of side chains, yielding SmA and Lam Col phases for ILCs with 2-3 chains and Col ro , Col h phases for ILCs with 3-6 chains. Thus, we demonstrated that thioethers are a useful design tool for ILCs with tailored properties.

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“…Besides the well-established protocols that make use of thiols (Scheme 1) [17–21], other methodologies employing different sulfur sources such as disulfides or silylsulfides have been described, which most of them involves metals, e.g., indium [22], copper [23], mercury [24], or organocatalysts [25].…”

Section: Introductionmentioning

confidence: 99%

Thiol-free chemoenzymatic synthesis of β-ketosulfides

Heredia

López-Vidal

Kurina-Sanz

et al. 2019

Beilstein J. Org. Chem.

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A preparation of β-ketosulfides avoiding the use of thiols is described. The combination of a multicomponent reaction and a lipase-catalysed hydrolysis has been developed in order to obtain high chemical diversity employing a single sulfur donor. This methodology for the selective synthesis of a set of β-ketosulfides is performed under mild conditions and can be set up in one-pot two-step and on a gram-scale.

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Sulfur makes the difference: synthesis and mesomorphic properties of novel thioether-functionalized imidazolium ionic liquid crystals

Cited by 10 publications

References 60 publications

Ionic Liquid Crystals: Versatile Materials

Ionic Liquid Crystals: Versatile Materials

Chasing Self‐Assembly of Thioether‐Substituted Flavylium Salts in Solution and Bulk State

Thiol-free chemoenzymatic synthesis of β-ketosulfides

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