Synthesis and characterization of luminescent tricationic salts of mesitylene and stilbazolium moieties

Jo, Tae Soo; McCurdy, William; Tanthmanatham, Ontida; Kim, Tae Kyoung; Han, Haesook; Bhowmik, Pradip K.; Heinrich, Benoît; Donnio, Bertrand

doi:10.1016/j.molstruc.2012.03.024

Cited by 11 publications

(11 citation statements)

References 51 publications

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“…TOSs have also been investigated for their possible photophysical properties. Bhowmik et al have reported on the luminescent behavior of some TOSs 84 (Scheme ), based on tosylate, [NTf 2 – ], AOT and methyl orange and having a mesitylene core containing trans ‐4‐octyloxy‐4′‐stilbazolium moieties 97…”

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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“…This result perfectly agrees with the observation previously reported in the literature about the decrease in melting temperature of ionic liquids induced by the presence of fluorine containing anions. 12,53,54 On the other hand, for dicarboxylate salts the melting temperature increases on going from 1,4-butanedicarboxylate (2h) up to 1,4-benzenedicarboxylate (2f ), outlining a certain influence on the analysed parameter of both the length (2h-i) and the nature of the spacer (2h and 2f ). In particular, Organic & Biomolecular Chemistry Paper the presence of an aromatic spacer, the distance between the charged heads being the same, induces a significant increase in melting temperature.…”

Section: Dsc Measurementsmentioning

confidence: 99%

“…[3][4][5][6][7][8][9] Tripositive cations are even scarcer. [10][11][12] The interest in dicationic ionic liquids is largely due to their high thermal stability, higher than that normally characterising the corresponding monocationic ionic liquids. This has recently allowed their use as media when high temperatures are required.…”

Section: Introductionmentioning

confidence: 99%

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

et al. 2013

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A new class of functionalised dicationic ionic liquids, containing a central cationic unit capped by a basic functionality (imidazole), has been synthesised. These salts have been characterised in isotropic solution using proton and 2D-NMR spectroscopy, and their thermal stability has been studied by DSC and TGA. All these novel salts contain the 1-(1-imidazolylmethyl)-3,5-di{1-(3'-octylimidazolylmethyl)}-benzene cation as a defining structural motif. Salts of both singly and doubly charged anions were prepared and, in particular, the selected monoanions (Br − , [BF 4 ] − , or [NTf 2 ] − ) differ in size, shape and hydrogenbonding ability, whereas the dianions differ in the nature of the spacer, such as 1,4-benzenedicarboxylate, 2,6-naphthalenedicarboxylate, 1,5-and 2,6-naphthalenedisulfonate, 1,4-butanedicarboxylate, and 1,6-hexanedicarboxylate. These ionic liquids exhibit the presence of different conformers in solution, whose distribution is affected by the nature of the anion. The nature of the anion also affects their thermal stability.

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“…This is due to the potential to change their structural features simply by: varying the nature of the cation and/or the anion; tuning them by introducing small structural changes in the constituting ions, or of the spacers separating them provides the opportunity to obtain materials with sets of desired properties suitable for different applications. They have been applied as a chemical anchorage on a solid support [10], starting materials for the synthesis of molecular devices [11,12], reaction media or catalysts, immobilization of catalysts [9], reaction media for high-temperature organic reactions [13,14], catalysts [15], receptors for anion recognition [16], low-molecular-weight gelators [17], fluorescent organic salts [18,19], energetic materials [20,21], for use in the preparation of solid films for organic electronic applications [22] and electrowetting materials [23]. Heteromolecules including imidazole, 1,10-phenanthroline, pyridine and others have been used as the starting materials for the synthesis of polycationic organic salts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of tetracationic organic salt from 4,4'-bipyridine

Abebe¹,

Atlabachew²

2018

Bull. Chem. Soc. Eth.

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ABSTRACT. This report describes the synthesis of a tetracationic organic salt from 4,4'-bipyridine and 1-bromooctane using 1,3-dibromopropane as a spacer just in three simple steps. A careful monooctylation of one of the nitrogen atoms of 4,4'-bipyridine using 1-bromoocatane followed by the dimeriztion using 1,3-dibromopropane as a linker resulted a tetracationic organic salt of formula [C3H6(C8Bipyr)2]Br4. 1 H and 13 C NMR, and CHN elemental analysis as well as ultra high vacuum spectroscopic technique (XPS) were employed to confirm the synthesis and the purity of this compound. This compound has demonstrated molar conductivity of 4320 S cm 2 mol -1 unexpected from a salt with 1:4 cation to anion ratio. It is expected that this salt would have potential applications in materials such as for low-molecular-weight gelators and the preparation of solid films for organic electronic applications.

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Synthesis and characterization of luminescent tricationic salts of mesitylene and stilbazolium moieties

Cited by 11 publications

References 51 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

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

Synthesis of tetracationic organic salt from 4,4'-bipyridine

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