Synthesis and properties of 1,3-dioxo-1 H -inden-2(3H)-ylidene fragment and (3-(dicyanomethylene)-5,5-dimethylcyclohex-1-enyl)vinyl fragment containing derivatives of azobenzene for holographic recording materials

Zariņš, Elmārs; Kokars, Valdis; Ozols, Andris; Augustovs, Pēteris

doi:10.1117/12.886598

Cited by 7 publications

(8 citation statements)

References 6 publications

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“…which could be grouped in three different classes with similar key molecular fragments: -dione (WE-3). They have been synthesized in our previous research 16 . These materials differ only by number and type of amorphous phase creating functional groups in the molecules.…”

Section: Investigated Compoundsmentioning

confidence: 99%

“…Additional insertion of azobenzene fragment in their structures makes them also possible to form holographic volume and surface relief gratings (SRG) after exposure to laser radiation. This physical phenomena could be used for information and holographic data storage [16][17] . Unfortunately, there is still no clear relation between compound organic structures and their thermal, glass-forming and optical properties.…”

Section: Introductionmentioning

confidence: 99%

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Thermal, glass-forming, nonlinear optical and holographic properties of "push-pull" type azochromophores with triphenyl moieties containing isophorene and pyranylidene fragments

et al. 2013

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Molecular organic compounds with electron donating fragment bounded through π-conjugated system with electron acceptor fragment, as well as with incorporated triphenyl groups in their molecules show potential for creating cheap and simple solution processable materials with nonlinear optical properties. Additional insertion of azobenzene fragment in their structures makes them also possible to form holographic volume and surface relief gratings (SRG) after exposure to laser radiation, which could be useful for holographic data storage. For these purposes polymers are generally used. However, their application is complicated and challenging task as in every attempt to obtain the same polymer it will have different physical properties. On the other hand, the synthetic procedure of molecular glasses is more simple as their structure and physical properties are strongly defined. Unfortunately, there is still no clear relation between compound organic structures and their thermal, glass-forming and optical properties. In order to investigate the above mentioned regularities, we have synthesized and investigated ten molecular glassy organic compounds with three different fragments as main backbones of the molecules: indene-1,3-dione (WE-1, WE-2, WE-3), isophorene (IWK-1D, IWK-2M, IWK-2D) and pyranylidene (DWK-2TB, ZWK-2TB, JWK-2TB, ZWK-3AZO). Compounds containing isophorene fragment in their molecules had the highest NLO efficiencies (d 33 up to 125.7 pm/V for IWK-2D) and also were the most effective holographic data storage compounds with holographic self diffraction efficiency 13% and holographic diffraction efficiency 20%, also for IWK-2D, but their thermal stability (T d from 288 o C to 295 o C) and glass transition (T g from 90 o C to 105 o C) values were just average. Pyranylidene type compounds had the highest thermal stability and highest glass transition (T g from 115 o C to 180 o C). But their ability to form and maintain amorphous structure were low and they had average NLO efficiencies (d 33 up to 66.2 pm/V for ZWK-2TB) and average holographic self diffraction efficiency 2% and holographic diffraction efficiency 8% for ZWK-3AZO. The molecules with just azobenzene fragment and indene-1,3-dione as electron acceptor has the lowest thermal (T d from 250 o C to 282 o C, T g from 70 o C to 98 o C) and also the lowest holographic properties with holographic diffraction and self diffraction efficiencies at 4% for WE-1 and lower for other compounds. Nevertheless, some of the investigated molecular glasses show potential as multifunctional optical materials.

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Section: Investigated Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thermal, glass-forming, nonlinear optical and holographic properties of "push-pull" type azochromophores with triphenyl moieties containing isophorene and pyranylidene fragments

et al. 2013

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“…The electron acceptor fragment containing derivatives of isophorene (3,5,5-trimethylcyclohex-2-enone) (compounds 37-39 in Fig.11) thus obtained are not always isolated from the reaction mixture [31,37]. Once they are formed, the electron donor fragment containing aromatic aldehyde is added in the mixture for further reaction with the aldehyde.…”

Section: Addition Of Electron Acceptor Fragments To Derivatives Of 4hmentioning

confidence: 99%

“…It is subjected to the Knoevenagel condensation reaction with malononitrile (28). However, 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile (61) which is formed during the reaction is not isolated because 4-(bis(2-(trityloxy)ethyl)amino) benzaldehyde (75) is added to the reaction mixture after 2 hours [31,37] for further reaction. 2-(3-(4-(Bis(2-(trityloxy)ethyl)amino)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile (IWK) was obtained in good yield after its separation and purification by liyquid column chromatography as described in [31].…”

Section: Preparation Of Molecular Glassesmentioning

confidence: 99%

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Zariņš¹,

Vembris²,

Kokars³

et al. 2012

Organic Light Emitting Devices

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“…The synthesis and characterizing data can be found in our previously published papers[7,[12][13][14][15][16].…”

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Triphenylmethyl and triphenylsilyl based molecular glasses for photonic applications

Rutkis

Traskovskis

2015

SPIE Proceedings

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Triphenylmethyl and triphenylsilyl structural fragments can be used to obtain glass forming, solution processable materials from polar chromophore molecules. Large number of compounds has been synthesized taking advantage of this approach, making it possible to identify some structure-property relations. Regarding the non-linear optical (NLO) properties of the given materials it is evident that triphenylmethyl groups help shielding unwanted NLO efficiency limiting dipolar interactions between polar chromophores in solid films. Chromophore stacking is still observed for compounds with large dipole momentum values. The glass transition temperatures of the compounds increase with the molecular weight for the studied material class, reaching values up to 130°C.

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Synthesis and properties of 1,3-dioxo-1 H -inden-2(3H)-ylidene fragment and (3-(dicyanomethylene)-5,5-dimethylcyclohex-1-enyl)vinyl fragment containing derivatives of azobenzene for holographic recording materials

Cited by 7 publications

References 6 publications

Thermal, glass-forming, nonlinear optical and holographic properties of "push-pull" type azochromophores with triphenyl moieties containing isophorene and pyranylidene fragments

Thermal, glass-forming, nonlinear optical and holographic properties of "push-pull" type azochromophores with triphenyl moieties containing isophorene and pyranylidene fragments

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Triphenylmethyl and triphenylsilyl based molecular glasses for photonic applications

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