• 한국염색가공학회지
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• 제26권2호
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• pp.143-149
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• 2014

The designed dye material, namely 2-(4-(9H-carbazol-9-yl)benzylidene) compound, was synthesized. After the reaction, the solid was filtered and purified by recrystalization with acetone/water. To confirm and analyze its synthesis and structural formation, the single crystal was prepared and its measurement was carried out. A yellow needle crystal of $C_{22}H_{13}N_3$ were made on a Rigaku R-AXIS RAPID diffractometer using graphite monochromated CuK${\alpha}$ radiation. All details were suggested and introduced to support and communicate this study.

• Bulletin of the Korean Chemical Society
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• 제32권11호
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• pp.3963-3966
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• 2011

A series of pyranopyrazoles, was efficiently synthesized via one-pot, four component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes and malononitrile in the presence of catalytic amount silicotungstic acid under solvent free condition. NOE experiments confirmed that the product exist exclusively in the 2H form. The present protocol offers the advantages of clean reaction, short reaction time, high yield, easy purification and economic availability of the catalyst.

• Bulletin of the Korean Chemical Society
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• 제33권8호
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• pp.2679-2682
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• 2012

A simple one-pot synthesis of two derivatives of 1,4-dihydropyridines has been described under reflux conditions using copper iodide nanoparticles (CuI NPs) as a catalyst in high yields. This method demonstrated four-component coupling reactions of aldehydes and ammonium acetate via two pathways. In one route, the reaction was performed using 2 eq ethyl acetoacetate while in the other one 1 eq ethyl acetoacetate and 1 eq malononitrile were used. The CuI NPs was reused and recycled without any loss of activity and product yield. It is noteworthy to state that wide range of the 1,4-dihydropyridines have attracted large interest due to pharmacological and biological activities.

• Bulletin of the Korean Chemical Society
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• 제34권7호
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• pp.2148-2154
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• 2013

Three push-pull organic semiconductors, TPA-$Th_3$-MMN (1), TPA-ThTT-MMN (2), and TPA-ThDTT-MMN (3), comprising a triphenylamine donor and a methylene malononitrile acceptor linked by various ${\pi}$-conjugated thiophene units were synthesized, and the effects of the ${\pi}$-conjugated bridging unit on the photovoltaic characteristics of solution-processed small-molecule organic solar cells based on these semiconductors were investigated. Planar bridging units with extended ${\pi}$-conjugation effectively facilitated intermolecular ${\pi}-{\pi}$ packing interactions in the solid state, resulting in enhanced $J_{sc}$ values of the SMOSCs fabricated with bulk heterojunction films.

• Bulletin of the Korean Chemical Society
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• 제35권6호
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• pp.1670-1674
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• 2014

Two red emitters, 2-(7-(4-(diphenylamino)styryl)-2-methyl-4H-chromen-4-ylidene)malonitrile (Red 1) and 2-(7-(julolidylvinyl)-2-methyl-4H-chromen-4-ylidene)malonitrile (Red 2) have been designed and synthesized for application as red-light emitters in organic light emitting diodes (OLEDs). In these red emitters, the julolidine and triphenyl moieties were introduced to the emitting core as electron donors, and the chrome-derived electron accepting groups such as 2-methyl-(4H-chromen-4-ylidene)malononitrile were connected to electron donating moieties by vinyl groups. To explore the electroluminescence properties of these materials, multilayered OLEDs using red materials (Red 1 and Red 2) as dopants in $Alq_3$ host were fabricated. In particular, a device using Red 1 as the dopant material showed maximum luminous efficiencies and power efficiencies of 0.82 cd/A and 0.33 lm/W at $20mA/cm^2$. Also, a device using Red 2 as a dopant material presented the CIEx,y coordinates of (0.67, 0.32) at 7.0 V.

• Bulletin of the Korean Chemical Society
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• 제29권2호
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• pp.335-338
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• 2008

New efficient red emitter having short p?-conjugation length and asymmetric bulky structure, 2-(7-diphenylamino-benzo[1,2,5]thiadiazole-4-ylmethylene)-malononitrile, was synthesized and characterized. Using this material as a dopant, we fabricated electroluminescence device with a structure of ITO/DNTPD/NPD/BTZA (5 wt% in Alq3)/Alq3/LiF/Al. The device exhibited a high brightness of 761 cd/m2 at a driving voltage of 4.8 V, and current efficiency is 0.75 cd/A. The Commission International de IEclairage (CIE) coordinates of the EL device were found to be (0.62, 0.37) at 10 mA/cm2.

• Bulletin of the Korean Chemical Society
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• 제32권6호
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• pp.1873-1878
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• 2011

Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4-dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate $[HO_3S(CH_2)_4MIM][HSO_4]$ (a Br${\o}$nsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level.

• Bulletin of the Korean Chemical Society
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• 제18권3호
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• pp.318-323
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• 1997

ο-(2-Vinyloxyethoxy)benzylidenemalononitrile (3a) and methyl ο-(2-vinyloxyethoxy)-benzylidenecyanoacetate (3b), m-(2-vinyloxyethoxy)benzylidenemalononitrile (4a), and methyl m-(2-vinyloxyethoxy)benzylidenecyanoacetate (4b) were prepared by the condensation of ο-(2-vinyloxyethoxy)benzaldehyde (1) and m-(2-vinyloxyethoxy)benzaldehyde (2) with malononitrile or methyl cyanoacetate, respectively. Bifunctional vinyl ether monomers 3a and 3b polymerized quantitatively with radical initiators in γ-butyrolactone solution at 65 ℃, while meta-isomers 4a and 4b gave lower yields of polymers under the same conditions. The polymers 5-6 obtained from the monomers 3-4 were insoluble in common solvents due to cross-linking. Under the same polymerization conditions ethyl vinyl ether polymerized well with model compounds ο-methoxybenzylidenemalononitrile 7a, methyl ο-methoxybenzylidenecyanoacetate 7b, m-methoxybenzylidenemalononitrile 8a, and methyl m-methoxybenzylidenecyanoacetate 8b, respectively, to give 1:1 alternating copolymers 9-10 in high yields. Cross-linked polymers 5-6 showed a thermal stability up to 300 ℃, and showed a double phase degradation pattern in their TGA thermograms. Polymers 5-6 showed broad endothermic bands around 75-110 ℃ without any characteristic Tg peaks in DSC thermograms. Alternating copolymers 9-10, except copolymer 9b were soluble in common organic solvents. The inherent viscosities of polymer 9-10 were in the range of 0.35-0.62 dL/g. Polymer films cast from acetone solution were cloudy and tough and Tg values obtained from DSC thermograms were in the range of 118-165 ℃.

• Bulletin of the Korean Chemical Society
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• 제17권3호
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• pp.257-262
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• 1996

p-(2-Vinyloxyethoxy)benzylidenemalononitrile 2 and methyl p-(2-vinyloxyethoxy)benzylidenecyanoacetate 3 was prepared by the condensation of p-(2-vinyloxyethoxy)benzaldehyde 1 with malononitrile or methyl cyanoacetate, respectively. Vinyl ether monomers 2 and 3 polymerized quantitatively with radical initiators in γ-butyrolactone solution at 65 ℃. The trisubstituted terminal double bond participated in the vinyl polymerization and radical polymerization of 2 and 3 led to swelling polymers 4 and 5 that were not soluble in common solvents due to cross-linking. Under the same polymerization conditions ethylvinyl ether polymerized well with model compounds of p-methoxybenzylidenemalononitrile 6 and methyl p-methoxybenzylidenecyanoacetate 7, respectively, to give 1:1 alternating copolymers 8 and 9 in high yields. Polymers 4 and 5 showed a thermal stability up to 300 ℃ without any characteristic Tg peaks in DSC thermograms. Alternating copolymers 8 and 9 were soluble in common solvents such as acetone and DMSO, and the inherent viscosities of the polymers were in the range of 0.36-0.74 dL/g. Films cast from acetone solution were cloudy and tough and Tg values obtained from DSC thermograms were in the range of 59-60 ℃.

• Bulletin of the Korean Chemical Society
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• 제25권10호
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• pp.1545-1550
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• 2004

meso-Functionalized dipyrromethanes 6-10 were synthesized by acid-catalyzed addition of pyrrole to ${\alpha}$-position of 2-alkenyl pyrroles. The regiochemistry of the reaction can be explained by either the formation of more stable carbocation intermediate or ${\beta}$-addition of ${\alpha},{\beta}$-unsaturated carbonyl compounds. The starting 2-alkenyl pyrroles were synthesized by Aldol condensation of 2-formylpyrrole with active methylene compounds such as nitromethane, diethylmalonate and malononitrile. Attempted ‘2+2' condensation of meso-diethylmalonyldipyrromethane, meso-(p-tolyl)dipyrromethane and p-tolualdehyde afforded three different porphyrins 12, 13 and 14 in reasonable yields. On the other hand, meso-(nitromethyl)dipyrromethane with p-(tbutyl) benzaldehyde resulted in the formation of three different porphyrins such as 5,15-dicyano-10,20-diarylporphyrin (16), 5-cyano-15-formyl-10,20-diarylporphyrin (17) and 5,15-diformyl-10,20-diarylporphyrin (18) in low yields. Conversion of nitromethyl groups to nitrile and (or) formyl group was observed under the porphyrin forming conditions.