• Polymer(Korea)
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• v.36 no.6
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• pp.776-788
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• 2012

Octa[8-{4-(4'-cyanophenylazo)phenoxy}]octyl and octa[8-{4-(4'-cyanophenylazo)phenoxycarbonyl}]heptanoated disaccharide derivatives were synthesized by reacting cellobiose, maltose, and lactose with 1-{4-(4'-cyanophenylazo) phenoxy}octylbromide or 1-{4-(4'-cyanophenylazo)phenoxycarbonyl}]heptanoyl chloride, and their thermotropic liquid crystalline and photochemical phase transition behavior were investigated. All the {(cyanophenylazo)phenoxy} octyl disaccharide ethers (CADETs) formed monotropic nematic (N) phases, whereas all the {(cyanophenylazo) phenoxycarbonyl}heptanoated disaccharide esters (CADESs) exhibited enantiotropic N phases. Compared with CADETs, CADESs showed higher isotropic (I)-to-N phase transition temperatures. Photoirradiation of the disaccharide derivatives in a glass cell or in a cell with a rubbed polyimide (PI) alignment layer at a N phase resulted in disappearance of the N phase due to trans-cis photoisomerization of azobenzene, and the initial N phase was recovered when the irradiated sample was kept in the dark because of cis-trans thermal isomerization and reorientation of trans-azobenzenes. The rates of the photochemical N-I and the thermal I-N phase transition of disaccharide derivatives in a cell with a rubbed PI alignment layer were faster than those in a glass cell, and were significantly different from those observed for the monomesogenic compounds containing cyanoazobenzene and the 4-{4'-(cyanophenylazo)phenoxy}octyl glucose and cellulose ethers. The results were discussed in terms of difference in cooperative motion of azobenzene groups due to the flexibility of the main chain, the number of mesogenic units per repeating units, and the distance between the azobenzene groups.

• Applied Chemistry for Engineering
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• v.26 no.6
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• pp.698-705
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• 2015

Two series of symmetric dimesogenic compounds containing a butylene or 1-methylbutylene spacer as a flexible group were synthesized. The mesogenic groups of synthesized compounds consist of an azobenzene group with a terminal substituent. Chemical structures as well as, thermal, mesomorphic, and photochemical properties of the synthesized compounds were investigated using FT-IR, $^1H-NMR$, differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and UV-visible spectrometry. P-H, P-F, and $P-OC_6H_{13}$ showed monotropic liquid crystal phases, whereas the others showed enantiotropic liquid crystal phases. Compounds with butylene group as a flexible spacer exhibited wider mesophase temperature ranges and higher thermal transition temperatures than compounds containing a 1-methylbutylene group. Compounds with a high absolute value of the Hammett substituent constant exhibited high thermal transition temperatures and improved stability in the liquid crystal phase. Furthermore, in the absence or presence of UV light illumination, terminal substituents of the azomesogenic group were important factors in deciding the maximum absorbance wavelength (${\lambda}_{max}$) and the rate of photoisomerization (K).

• Applied Chemistry for Engineering
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• v.30 no.2
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• pp.247-253
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• 2019

In this study, compounds with azo-mesogenic groups at 4-, 3,5-, or 3,4,5-positions of one phenyl ring were synthesized, and their liquid crystallinity and photochemistry were investigated. The compounds in the Azo1 and Azo2 series had linear and planar geometries, respectively, while those in the Azo3 series had relatively bulky structures. Compounds of BA-Azo2 and BA-Azo3 did not show any liquid crystallinity. Compounds of BE-Azo1 and BE-Azo2 exhibited a monotropic liquid crystallinity, while the other compounds showed an enantiotropic liquid crystallinity. The liquid crystalline behavior was imparted by the azo-mesogenic groups, and most of the liquid crystalline compounds formed a smectic phase. All the RM-AzoX compounds exhibited photoisomerism because of the presence of the azo groups in the molecule. The rate of photoisomerization followed the order of RM-Azo3 < RM-Azo1 < RM-Azo2 and was considered to depend on the steric hindrance around the azobenzene groups in the molecule. These results suggest that the liquid crystallinity and photochemical property of the compounds are affected by the position or the number of azo-mesogenic groups phenyl ring of the molecule.

• Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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• 2006.11a
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• pp.166-167
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• 2006

Dendrimers represent a new class of synthetic macromolecules characterized by a regularly branched treelike structure. Multiple branching yields a large number of chain ends that distinguish dendrimers from conventional star-like polymers and microgels. The azobenzene dendrimer is one of the dendrimeric macromolecules that include the azo-group exhibiting a photochromic character. Due to the presence of the charge transfer element of the azo-group and its rod-shaped structure, these compounds are expected to have potential interest in electronics and photoelectronics, especially in nonlinear optics. In the present paper, we give pressure stimulation to organic thin films and detect the induced displacement current. Functional photoisometrization organic molecular the photo-stimulus to organic monomolecular L-films and LB films of dendrimer and 8A5H were performed. The 8A5H organic monolayer in case of pressure stimulus occurred that positive course but in case of the photo-stimulus compared positive and negative. It is assumed that generation forms of displacement current were measured when photo-stimulus for Impression.

• KIEE International Transactions on Electrophysics and Applications
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• v.5C no.1
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• pp.28-32
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• 2005

In the Langmuir-Blodgett (LB) technique, a monolayer on the water surface is transferred onto a substrate, which is raised and dipped through the surface. From this, multilayers can be obtained in which constituent molecules are periodically arranged. The LB technique has attracted considerable interest in the fabrication of electrical and electronic devices. Many researchers have investigated the electrical properties of monolayer and multiplayer films. Dendrimers represent a new class of synthetic macromolecules characterized by a regularly branched treelike structure. Multiple branching yields a large number of chain ends that distinguish dendrimers from conventional star-like polymers and microgels. The azobenzene dendrimer is one of the dendritic macromolecules that include the azo-group exhibiting a photochromic character. Due to the presence of the charge transfer element of the azo-group and its rod-shaped structure, these compounds are expected to have potential interest in electronics and ptoelectronics, especially in nonlinear optics. In the present paper, we give pressure stimulation to organic thin films and detect the induced displacement current.

• Journal of the Korean Chemical Society
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• v.27 no.3
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• pp.213-217
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• 1983

Devices that mimic the natural photosynthetic pathway are of considerable interest as fuel sources. Quantum yield of viologen radical formation in several water-in-oil microemulsion system were measured. The yield of hexadecylviologen radical formation in microemulsion system using EDTA as an electron donor, ruthenium bipyridinium complex as photosensitizer, and hexadecylviologen as an electron acceptor was 12%. When benzylnicotinamide was inserted in the interface of the microemulsion and azo compound was dissolved in oil face, the quantum yield of hydroazo compound was 0.16. Organic dye (Rose bengal) was used as photosensitizer for the photoinduced electron transfer reaction. In anionic microemulsion no electrontransfer was observed.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.19 no.8
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• pp.724-731
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• 2006

We investigated the electrochemical properties for Langmuir-Blodgett (LB) films mixed with 4-octyl-4'-(5-carboxylpentamethyleneoxy)azobenzene (denoted as 8A5H) and phospholipid(L-a-dimyristoylphosphatidylcholine, denoted as DMPC and L-a-dilauroylphosphayidylcholine, denoted as DLPC). The LB films of 8A5H, 8A5H-DMPC and 8A5H-DLPC mixture monolayers were deposited by using the LB method on the indium tin oxide(ITO) glass. The electrochemical properties measured by using cyclic voltammetry with a three-electrode system, an Ag/AgCl reference electrode, a platinum wire counter electrode and LB film-coated ITO working electrode at various concentrations(0.1, 0.5, and 1.0 mol/L) of $NaClO_4$ solution. A measuring range was reduced from initial potential to -1350 mV, continuously oxidized to 1650 mV and measured to the initial point. The scan rates were 50, 100, 150 and 200 mV/s, respectively. As a result, LB films of 8A5H and 8A5H-DLPC mixture monolayers appeared irreversible process caused by only the oxidation current from the cyclic voltammogram and LB films of 8A5H-DMPC monolayer mixture was found to be caused by a reversible oxidation-reduction process.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.13 no.4
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• pp.318-325
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• 2000

Dynamic behaviors of saturated-fatty acids $C_{16}$, $C_{18}$, $C_{20}$ and 8A5H with azobenzene were measured by displacement current method when the molecules are stimulated by pressure light and heat. When a barrier was compressed I-A, $\pi$-A isotherms of $C_{16}$, $C_{18}$, and $C_{20}$ were similar to each other but the displacement current of $C_{20}$ which has a long alkyl chain was relatively low. 8A5H showed the form of double liquid films and had a reversible reaction when a barrier was compressed and then expanded. When the molecules of 8A5H were stimulated by 365[nm] light the positive currents which were generated by the structural changes from trans to cis were measured. But the negative currents of the structural changes from cis to trans by 450[nm] light were too weak to detect. When the temperature of the water subphase was increased the surface pressures of the monolayers were increased early because of the thermal activations of the molecules and the double liquid films of 8A5H were disappeared above 40[$^{\circ}C$]EX>].

• Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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• 2006.05a
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• pp.52-54
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• 2006

In the Langmuir-Blodgett (LB) technique, a monolayer on the water surface is transferred onto a substrate, which is raised and dipped through the surface. From this, multi layers can be obtained in which constituent molecules are periodically arranged. The LB technique has attracted considerable interest in the fabrication of electrical and electronic devices. Many researchers have investigated the electrical properties of monolayer and multiplayer films. Dendrimers represent a new class of synthetic macromolecules characterized by a regularly branched treelike structure. Multiple branching yields a large number of chain ends that distinguish dendrimers from conventional star-like polymers and microgels. The azobenzene dendrimer is one of the dendritic macromolecules that include the azo-group exhibiting a photochromic character. Due to the presence of the charge transfer element of the azo-group and its rod-shaped structure, these compounds are expected to have potential interest in electronics and ptoelectronics, especially in nonlinear optics. In the present paper, we give pressure stimulation to organic thin films and detect the induced displacement current.

• Bulletin of the Korean Chemical Society
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• v.26 no.8
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• pp.1170-1176
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• 2005

The structures and conformations of ortho-, meta-, and para-methyl red (MR) upon proton gain and loss were studied by density functional calculations, and compared to methyl yellow for the effects of a carboxyl substitution. Internal hydrogen bonding causes the geometry of neutral o-MR planar, otherwise twist. Monoprotonated species of MR are planar where the proton is attached to $\beta$-azo nitrogen. This loses its azo character a bit, and shows strong delocalization characterized as a quinonoid canonical structure. Di-protonated species of MR is proved to hold two protons at the amino and $\alpha$-azo nitrogen atoms, and planar. It regains somewhat of its azo character, but still shows fairly delocalized property in terms of carbocationic canonical structures. The carboxyl substitution on 4-dimethylamino-trans-azobenzene structure has some delocalization effects on the geometry or conformation of MR derivatives whether neutral, mono-, di- or de-protonated.