• Bulletin of the Korean Chemical Society
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• v.27 no.3
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• pp.345-354
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• 2006

Ionic liquids are alternative reaction media of increasing interest and are regarded as an eco-friendly alternatives, of potential use in place of the volatile organic solvents typically used in current chemical processing methods. They are emerging as the smart and excellent solvents, which are made of positive and negative ions that they are liquids near room temperature. The nucleophilic substitution reaction is one of the important method for inserting functional groups into a carbon skeleton. Many nucleophilic substitution reactions have been found with enhanced reactivity and selectivity in ionic liquid. In this review, some recent interesting results of nucleophilic substitution reactions such as hydroxylations, ether cleavages, carbon-X (X= carbon, oxygen, nitrogen, fluorine) bond forming reactions, and ring opening of epoxides in ionic liquids are discussed.

• Bulletin of the Korean Chemical Society
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• v.31 no.6
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• pp.1785-1788
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• 2010

• Proceedings of the Materials Research Society of Korea Conference
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• 2011.05a
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• pp.244.2-244.2
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• 2011

We introduce a novel and robust method for the preparation of nanocomposite multilayers, which allows the excellent photoluminescent (PL) properties as well as the accurate control over the composition and dimensions of multilayers. By exchanging the oleic acid stabilizers of CdSe@ZnS quantum dots (QDs) synthesized in organic solvent with 2-bromo-2-methylpropionic acid (BMPA) in the same solvent, these nanoparticles were be alternately deposited by nucleophilic substitution reaction with highly branched poly(amidoamine) dendrimer (PAMA) through layer-by-layer (LbL) assembly process. Our approach does not need to be transformed into the water-dispersible nanoparticles with electrostatic or hydrogen-bonding groups, which can deteriorate their inherent properties, for the built-up of multilayers. The nanocomposite multilayers including QDs exhibited the strong PL properties achieving densely packed surface coverage as well as long-term PL stability under atmospheric conditions in comparison with those of conventional LbL multilayers based on electrostatic interaction. Furthermore, we demonstrate that the flexible multilayer films with optical properties can be easily prepared using nucleophilic substitution reaction between bromo and amino groups in organic media. This robust and tailored method opens a new route for the design of functional film devices based on nanocomposite multilayers.

• Bulletin of the Korean Chemical Society
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• v.11 no.1
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• pp.65-69
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• 1990

The nucleophilic substitution reactions of naphthalene-1,5-disulfonyl chloride and 4-fluorosulfonylbenzenesulfonyl chloride with p-substituted anilines and methyl substituted pyridines in methanol-acetonitrile mixtures and hydrolyses of those disulfonyl halides have been studied by means of conductometric and polarographic methods. A large difference in the selective parameter, ${\rho}_N$ between mono-sulfonyl chloride and disulfonyl halide can be taken as an evidence that the second $SO_2Cl$ grolup of naphthalene-1,5-disulfonyl chloride also takes part in the reaction in contrast to sulfonyl fluoride in 4-fluorosulfonylbenzenesulfonyl chloride, which only acts as a substituent in the nucleophilic substitution reaction.

• Journal of the Korean Magnetic Resonance Society
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• v.22 no.4
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• pp.115-118
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• 2018

Dipyrromethane 2 functionalized with 3-chloropropyl group on the meso carbon undergoes an unusual intramolecular electrophilic aromatic substitution reaction in the presence of $NaN_3$ instead of a simple nucleophilic substitution reaction. As a result, a new chiral dipyrromethane 1 was synthesized. In this reaction, the ${\beta}$-carbon of the pyrrole ring functions as a nucleophile while the carbon next to the chlorine atom acts as an electrophile. Interestingly, this reaction progresses even in the absence of an acid catalyst. Compound 1 was fully characterized by $^1H-^1H$ and $^1H-^{13}C$ COSY NMR spectroscopic analyses and the high resolution EI mass spectrometry.

• Bulletin of the Korean Chemical Society
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• v.12 no.3
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• pp.295-301
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• 1991

The nucleophilic substitution reactions of p-substituted benzenesulfonyl chlorides wiht p-substituted anilines were carried out in 1,1,1,3,3,3-hexafluoro-2-propanol and 2-propanol mixtures. The salt effect was observed to be inhibited by the reaction of 1,1,1,3,3,3-hexafluoro-2-propanol with nucleophiles. To investigate the effectiveness of the salt for the nucleophilic substitution reaction the relative salt effect was determined. According to the comparison with the inhibitive salt effect and the substituent effects for the substrates and nucleophiles, the reactions were predicted to be controlled by the salt effect more than substituent effect in HFP-PrOH mixtures.

• Journal of the Institute of Electronics Engineers of Korea SD
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• v.43 no.2 s.344
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• pp.13-17
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• 2006

Pentacene channel for organic thin film transistor was deposited on the SiOC film by thermal evaporation. The growth of pentacene is related with the Diels-Alder reaction and the nucleophilic reaction by the thermal induction. The surface is an important factor to control the recursive Diels-Alder reaction for growing of pentacene on SiOC far The terminal C=C double bond of pentacene molecule was broken easily as a result of attack of the nucleophilic reagents on the surface of SiOC film. The nucleophilic reaction can be accelerated by increasing temperature on surface, and it maks pentacene to grow hardly on the SiOC film with a flow rate ratio of $O_2/(BTMSM+O_2)=0.5$ due to its inorganic property. The nucleophlic reaction mechanism is $SN_2(bimolecular nucleophilic substitution)$ type.

• Journal of Photoscience
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• v.2 no.2
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• pp.77-81
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• 1995

Photoreactions of pseudosaccharin ethers have been investigated. Pseudosaccharin 3-allyl ether undergoes a facile photoreaction via reaction pathways involving homolysis of bond between pseudosaccharyl oxygen and 3-allyl carbon, and excited nucleophilic substitution of allyloxy group by solvent which are not quenched by oxygen present in the reaction. Product yield demonstrates that the homolysis pathway predominates over the nucleophilic substitution in ca. 7:1 ratio. In contrast, pseudosaccharin alkyl ethers follow different reaction routes to produce two products, solvent-substituted pseudosaccharin alkyl ethers and reduction products, 3-alkoxy-1, 2-benzisothiazoles. The formations of reduction products, 3-alkoxy-1, 2-benzisothiazoles are completely quenched by oxygen.

• Bulletin of the Korean Chemical Society
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• v.28 no.12
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• pp.2535-2538
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• 2007

• Bulletin of the Korean Chemical Society
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• v.6 no.3
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• pp.162-164
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• 1985

Nucleophilic substitution reaction of dansyl chloride with anilines in various solvents have been investigated. The Bronsted ${\beta}$ and Hammett ${\rho}_N$ values indicated that the bond formation is advanced more than the bond breaking at the transition state. Solvatochromic correlations also predicted the importance of bond formation at the TS, showing a greater contribution of polarity (${\pi}^{\ast}$) compared to hydrogen bond donor acidity (${\alpha}$). The effect of solvent on rate was found to violate the reactivity-selectivity principle.