Discotic liquid crystalline materials for potential nonlinear optical applications: synthesis and liquid crystalline behavior of 1,3,5-triphenyl-2,4,6-triazine derivatives containing achiral and chiral alkyl chains at the periphery

Lee, Hyoyoung; Kim, Dongwoo; Lee, Hyung-Kun; Qiu, Weibin; Oh, Nam-Keun; Zin, Wang‐Cheol; Kim, Kimoon

doi:10.1016/j.tetlet.2003.11.085

Cited by 76 publications

(44 citation statements)

References 39 publications

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“…Recently, coupling reactions of organometallic reagents with cyanuric chloride 101a (Scheme 21), direct [280] and palladium-catalyzed [255,281,282], have become the preferred way.…”

Section: Compounds With Heterocyclic Coresmentioning

confidence: 99%

Star-Shaped Conjugated Systems

2010

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The present review deals with the preparation and the properties of star-shaped conjugated compounds. Three, four or six conjugated arms are attached to cross-conjugated cores, which consist of single atoms (B, C+, N), benzene or azine rings or polycyclic ring systems, as for example triphenylene or tristriazolotriazine. Many of these shape-persistent [n]star compounds tend to π-stacking and self-organization, and exhibit interesting properties in materials science: Linear and non-linear optics, electrical conductivity, electroluminescence, formation of liquid crystalline phases, etc.

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“…Recently, coupling reactions of organometallic reagents with cyanuric chloride 101a (Scheme 21), direct [280] and palladium-catalyzed [255,281,282], have become the preferred way.…”

Section: Compounds With Heterocyclic Coresmentioning

confidence: 99%

Star-Shaped Conjugated Systems

2010

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“…[7] The same substitution in some other discogens transforms the columnar hexagonal (Col h ) to a columnar rectangular (Col r ) phase. [11] Recently, we demonstrated that substituted triphenyl derivatives of verdazyl, a π-delocalised radical, form discotic hexagonal phases. [12][13][14] We have investigated three series of compounds containing 3,4,5-trialkoxyphenyl [12] (such as 1a), 3,4,5-trialkylsulfanylphenyl [13] and a mixture of both substituents.…”

Section: Introductionmentioning

confidence: 99%

Chiral discotic derivatives of 1,3,5-triphenyl-6-oxoverdazyl radical

et al. 2014

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Two derivatives of 1,3,5-aryl-6-oxoverdazyl containing two 3,4,5-trioctyloxyphenyl and one 3,4,5-tri((S)-3,7-dimethyloctyloxy)phenyl group in position C(3) (1b) or N(1) (1c) were investigated by thermal, X-ray diffraction and magnetic methods. The results were compared to those obtained for achiral derivative 1a containing three 3,4,5-trioctyloxyphenyl groups. All three compounds exhibit an ordered columnar hexagonal phase, Col h(o) , and for chiral derivatives, 1b and 1c, a superstructure with doubled periodicity was found. The introduction of the three chiral alkoxy substituents in 1a lowered the mesophase stability by about 50 K and induced a Col h phase in 1c. Thermochromic analysis showed a hypsochromic shift upon formation of the Col h(o) phase similar for all three derivatives 1 (~0.3 eV), which coincides with a 5% drop in effective magnetic moment, μ eff , for 1c. Analysis of magnetisation data in a range of 2-370 K at 200 Oe revealed weak antiferromagnetic interactions (θ = -4 K) in the Col h(o) phase.

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“…The residue was then chromatographed over silica gel (Wakogel C-300, 2 % MeOH/CH 2 Cl 2 ) to give 5-bromo-1,3-bis-TEG-benzene (418.8 mg, 74 %) as a colorless oil. R f = 0.33 (EtOAc 5-Bromo-1,2,3-tris-TEG-benzene: Pulverized K 2 CO 3 (2.30 g, 16.7 mmol) was added to a DMF solution (18 mL) of 5-bromo-1,2,3-trihydroxybenzene [29] (600.5 mg, 2.9 mmol) and triethyleneglycol (TEG) toluene-4-sulfonate (3.21 g, 10.1 mmol), and the system was stirred under nitrogen at 50 8C for 33 h. The mixture was allowed to cool and poured into a separating funnel together with water (25 mL), and the aqueous solution was extracted with CH 2 Cl 2 . The combined extracts were dried over anhydrous MgSO 4 , and DMF was removed in vacuo to give an oil.…”

Section: Methodsmentioning

confidence: 99%

Solvent‐Assisted Organized Structures Based on Amphiphilic Anion‐Responsive π‐Conjugated Systems

Maeda

Ito

Haketa

et al. 2009

Chemistry A European J

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The synthesis of amphiphilic pi-conjugated acyclic oligopyrroles and the formation of solvent-assisted aggregates are reported. We have prepared various types of BF(2) complexes of 1,3-dipyrrolylpropane-1,3-diones bearing aryl rings substituted with hydrophilic polyethyleneglycol (PEG) chains, both as acyclic anion receptors and as building subunits for organized architectures based on pi-pi stacking. The formation of supramolecular H-type assemblies of these "amphiphilic" derivatives in aqueous solution was suggested by UV/Vis and fluorescence spectroscopy and further supported by (1)H NMR and dynamic light scattering (DLS) analyses. Cryogenic transmission electron microscopy (cryo-TEM) analyses of the aqueous solutions suggest that the fabrication of nanoscale network structures and vesicles depends on the peripheral substituents. The H-aggregates in aqueous solution are sensitive to the conditions required for transformation into monomers through replacement with miscible solvents such as alcohols and into J-type aggregates by water evaporation and freeze-drying procedures. However, they are fairly stable and sustainable to anion binding, whereas on CH(2)Cl(2) extraction they are transformed into other assembled modes but remain in the aqueous solution. The metastable states of affairs for distributions between two immiscible solvents are controlled by the orders of solution preparation; this also suggests that the formation of stable assemblies is assisted by water molecules. Furthermore, assemblies in which the stacking modes depend on the aliphatic side chains are also observed in a nonpolar hydrocarbon solvent.

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Discotic liquid crystalline materials for potential nonlinear optical applications: synthesis and liquid crystalline behavior of 1,3,5-triphenyl-2,4,6-triazine derivatives containing achiral and chiral alkyl chains at the periphery

Cited by 76 publications

References 39 publications

Star-Shaped Conjugated Systems

Star-Shaped Conjugated Systems

Chiral discotic derivatives of 1,3,5-triphenyl-6-oxoverdazyl radical

Solvent‐Assisted Organized Structures Based on Amphiphilic Anion‐Responsive π‐Conjugated Systems

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