Columnar bis(pyridinium) ionic liquid crystals derived from 4-hydroxypyridine: synthesis, mesomorphism and emission properties

Pană, Amalia; Iliş, Monica; Staicu, Teodora; Pasuk, Iuliana; Cı̂rcu, Viorel

doi:10.1080/02678292.2015.1116630

Cited by 9 publications

(11 citation statements)

References 56 publications

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“…The new monodentate ligands having three alkoxyl chains with variable number of carbon atoms were prepared through the reaction of 4‐hydroxypyridine with 3,4,5‐tris(alkyloxy)benzyl bromide derivatives in THF in the presence of NaOH and tetrabutylammonium bromide (TBABr) as phase‐transfer catalyst to give 4‐pyridone derivatives PyO‐ n as the main product in 65–70 % yield (Scheme ) . All N ‐alkylated 4‐pyridone derivatives were fully characterized by 1 H and 13 C NMR and IR spectroscopy as well as by elemental analysis.…”

Section: Resultsmentioning

confidence: 99%

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Wide‐Range Columnar and Lamellar Photoluminescent Liquid‐Crystalline Lanthanide Complexes with Mesogenic 4‐Pyridone Derivatives

Chiriac

Pasuk

Secu

et al. 2018

Chemistry A European J

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A series of liquid crystals with various lanthanide ions (Eu , Sm , and Tb ) was designed and prepared starting from the corresponding lanthanide nitrates and N-alkylated 4-pyridone derivatives bearing mesogenic 3,4,5-tris(alkyloxy)benzyl moieties (alkyl=hexyl, octyl, decyl, dodecyl, tetradecyl, or hexadecyl). These new lanthanidomesogens were investigated for their mesogenic properties by a combination of differential scanning calorimetry, polarizing optical microscopy, and temperature-dependent powder X-ray diffraction (XRD). Their thermal stability was assessed by thermogravimetric analysis. All of these complexes show enantiotropic liquid-crystalline behavior with lamellar (SmA) phases in the case of shorter-chain complexes (C and C ) or hexagonal columnar phases (Col ) for complexes with longer alkyl chains (C , C , and C ), which were assigned on the basis of their characteristic textures and XRD studies. For complexes with an intermediate number of carbon atoms in the side chains (C ), both a lamellar phase at lower temperatures and a Col phase at higher temperatures were evidenced. In the solid state, all these complexes show characteristic emissions assigned to the corresponding lanthanide ion. In addition, the luminescence decay curves showed single-exponential decays with characteristic times in the millisecond range (0.75-0.90 ms for Eu , 0.045-0.060 ms for Sm , and 0.75-1.05 ms for Tb ).

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Section: Resultsmentioning

confidence: 99%

“…The PyO‐ n ( n =6, 8, 10, 12, 14, 16) ligands were prepared by a slightly modified known procedure . A 2 n aqueous solution of sodium hydroxide was added to a solution of 4‐hydroxypyridine and tetrabutylammonium bromide (phase‐transfer catalyst) in THF.…”

Section: Methodsmentioning

confidence: 99%

Wide‐Range Columnar and Lamellar Photoluminescent Liquid‐Crystalline Lanthanide Complexes with Mesogenic 4‐Pyridone Derivatives

Chiriac

Pasuk

Secu

et al. 2018

Chemistry A European J

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“…Their solid-state emission is significantly red shifted by comparison to solution emission spectra recorded in dichloromethane, suggesting a more complex emission mechanism, probably an aggregate-type emission in solid state [62].…”

Section: '-Bipyridinium-based Ionic Liquid Crystalsmentioning

confidence: 95%

“…, were reported recently [62]. While there are numerous examples of dicationic pyridinium ILC, this one represents the first example of this type.…”

Section: '-Bipyridinium-based Ionic Liquid Crystalsmentioning

confidence: 99%

Ionic Liquid Crystals Based on Pyridinium Salts

Cı̂rcu¹

2017

Progress and Developments in Ionic Liquids

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“…Then, the organic layer was dried using magnesium sulphate, concentrated and puried using chromatography to afford pure 4-(4-bromophenyl)pyridine (112). Ethynyltrimethylsilane (113) in Et 3 N was added to DMF solvent containing 4-(4-bromophenyl)pyridine (112), CuI, Pd(PPh 3 ) 4 , and PPh 3 in dry Et 3 N at room temperature. The reaction mixture was stirred at 60 C for 8 h under nitrogen atmosphere.…”

Section: Pyridine-based Molecules As Thermotropic Mesogensmentioning

confidence: 99%