• Analytical Science and Technology
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• v.10 no.1
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• pp.60-65
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• 1997

Solvent extraction of alkali metal and alkaline earth metal cations by mono-crown ether(benzo-15-crown-5) and bis-(crown ether)s(ethylenediamine bis(4'-formyl benzo-15-crown-5)) containing benzo-15-crown-5 moieties were investigated with water-chloroform system at $25^{\circ}C$. The order of the extraction equilibrium constants($K_e$) and the complexation constants($K_c$) for the alkali metal and alkaline earth metal cations with mono-crown ether and bis-(crown ether)s were Ca(II)>Na(I)>Sr(II)>K(I)>Mg(II)>Rb(I) and Sr(II)>Ca(II)>K(I)>Rb(I)>Mg(II)>Na(I) respectively. These results were explained in terms of the size effect of metal cation and electron density effect. Also, the bis-(crown ether)s was found to extract metal cations more effectively than the corresponding mono-crown ether.

• Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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• 2003.08a
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• pp.110-113
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• 2003

We report herein synthetic results obtained six new types of bis-benzocrown ethers containing imine group. Bis crown ethers l~3 are aminobenzo-15-crown-5-ether linked with terephthalaldehyde, isophthalaldehyde, phthaldehyde respectively by imine reaction. Bis crown ethers l~3 are different distances in each crown ether rings. Bis crown ether 4 has large cavity in crown ethers. Functionalized crown ether 5 is synthesized amonobenzo-l5-crown-5-ether and terephthaladehyde same ratio at one to one. Bis crown ether 6 has phothosensitive linkage between crown ethers. Bis crown ether 7 is prepared by amonobenzo-l5-crown-5-ether and triethyl ortho formate. 4'-Nitrobenzo-crown ethers and 3',4'-dinitrobenzo-crown ethers were prepared by nitration of benzo crown ethers, obtained from the reaction of catechol and oligoethylene glycol ditosylate. Crown ethers containing aldehyde group were synthesized from the reaction of 3,4-dihydroxybenzaldehyde and corresponding ditosylate respectively. The synthesized crown ethers were characterized respectively by IR, NMR. GC-Mass.

• Journal of the Korean Society of Industry Convergence
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• v.6 no.1
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• pp.73-80
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• 2003

We report herein synthetic results obtained six new types of bis-benzocrown ethers containing imine group. Bis crown ethers1~3 are aminobenzo-15-crown-5-ether linked with terephthalaldehyde, isophthalaldehyde, phthaldehyde respectively by imine reaction. Bis crown ethers1~3 are different distances in each crown ether rings. Bis crown ether 4 has large cavity in crown ethers. Functionalized crown ether 5 is synthesized amonobenzo-15-crown-5-ether and terephthaladehyde same ratio at one to one. Bis crown ether 6 has photosensitive linkage between crown ethers. Bis crown ether 7 is prepared by amonobenzo-15-crown-5-ether and triethyl ortho formate. 4'-Nitrobenzo-crown ethers and 3',4'-dinitrobenzo-crown ethers were prepared by nitration of benzo crown ethers, obtained from the reaction of catechol and oligoethylene glycol ditosylate. Crown ethers containing aldehyde group were synthesized from the reaction of 3,4-dihydroxybenzaldehyde and corresponding ditosylate respectively. The synthesized crown ethers were characterized respectively by IR, NMR, GC-Mass.

• Bulletin of the Korean Chemical Society
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• v.27 no.6
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• pp.893-898
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• 2006

Novel bis- and tris-crown ethers were synthesized from 1-aza and diaza-crown ethers with 2-acryloyloxy-methyl crown ethers through Michael addition. The synthesized bis- and tris-crown ethers were characterized by their elemental analyses, $^1H$-NMR, $^{13}C$-NMR, mass spectra, IR spectra, respectively. The complexation behavior of the bis- and tris-crown ethers with $Li^+$, $Na^+$, $Na^+$, $Rb^+$, $Cs^+$ was examined by $^1H$-NMR, FAB mass, and UV spectrometry.

• Journal of the Korean Chemical Society
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• v.40 no.9
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• pp.635-639
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• 1996

New bis-crown ether containing siloxane chain was synthesized. 1,3-Bis(trimethylsiloxy)-1,3-dimethyl-1,3-di(4'-ethylbenzo-18-crown-6) disiloxane (1) was synthesized by reaction of 4'-vinylbenzo-18-crown-6 with 1,3-bis(trimethylsiloxy)-1,3-dimethyl-1,3-disiloxane in the presence of Pt catalyst. 4'-Vinylbenzo-18-crown-6 was prepared through five-step reaction which started from the reaction of catechol and acetic anhydride.

• Bulletin of the Korean Chemical Society
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• v.20 no.5
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• pp.556-558
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• 1999

Lead-selective PVC membrane electrodes based on newly synthesized bis(crown ether)s containing 18-crown-6 moiety was prepared using standard PVC membrane composition. In order to monitor lead in environmental samples by lead sensor, especially good selectivity over alkali and alkaline earth metals has to be obtained. Thus, responses of the PVC membrane prepared with new bis(crown ether)s and Fluka ionophore V (crown ether) base to various cations include lead, alkali and alkaline earth metal ions were investigated for their use as a lead sensor. The polymeric liquid membrane based on trans-1 8-crown-6 ether exhibits the best overall potentiometric performances as a lead-selective electrode in terms of a wide linear dynamic range (between 10-6 and 10-2 M, Pb2+), excellent detection limit (less than 10-6 M) and good durability within limited error. The preferences of lead over other cations, such as Ag+, Hg2+, Na+, Ca2+ and even K+ in the aforementioned electrode are much better than the Fluka ionophore V system.

• Journal of the Korean Chemical Society
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• v.32 no.1
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• pp.71-78
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• 1988

The crown ether ring of 20, 21, 24, 25-tetranitrodibenzo-18-crown-6(TNDB-18-C-6) was cleaved by various alcoholic bases to give 2,4,5-trialkoxynitrobenzene derivatives and 4,5-dialkoxy-1,2-dinitrobenzene derivatives as the major products, and bis[(alkoxynitrophenoxy)ethyl]ether derivatives from partially cleaved crown ether ring as the minor products. The ring cleavage reaction of TNDB-18-C-6 with ethylene glycolic base resulted ring contraction through intramolecular nucleophilic cyclization of the initially formed ring cleavage product to give nitro derivatives of DB-14-C-4.

• Polymer(Korea)
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• v.30 no.5
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• pp.426-431
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• 2006

Novel azacrown ether containing blue -light emitting anthracene fluorophore, 9,10-bis [p-(1-aza-18-crown-6)methylphenyl] anthracene (3) and N,N-bis [9-(p-methylphenyl) anthracenyl-methyl] -1,6-diaza-18-crown-6 (4) were prepared by reacting anthracene derivatives 1 and 2 with mono- and diaza-18-crown-6, respectively Also, crown ether containing fluorophore copolymer (5) were prepared by reacting 1,6-diaza-18-crown-6 with 1. Their fluorescence emission spectral studies were investigated by binding group I, group II and various metal cations. The fluorophores showed an absorption at ${\lambda}_{max}$= 372 nm and an emission at ${\lambda}_{max}$= 430 nm. pH Dependency of fluorescence emission intensity were examined to determine the optimum pH for the fluorophores.

• Journal of the Korean Applied Science and Technology
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• v.22 no.3
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• pp.219-227
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• 2005

Competitive solvent extraction of the mixure of alkali metal and alkaline earth cation from water into organic solvent containing the crown ether carboxylic acid and anlogous crown ether phosphonic acid was investigated as follows. The lipophilic group is found to strongly influence to the selective extraction in the mixed systems from only alkali metal cation for sym-(n-decyldibenzo)-16-crown-5-oxyacetic acid $\underline{1}$ to mostly alkaline earth metal cation for sym-bis[4(5)-tert-butylbenzo]-16-crown-5-oxyacetic acid $\underline{3}$. Monoethyl sym-(n-decyldibenzo)-16-crown-5-oxymethylphosphonic acid $\underline{2}$. and monoethyl-sym- bis]4(5)-tert-butylbenzo]-16-crown-5-oxymethylphosphonic acid $\underline{4}$ showed good selectivity for $Na^+$ over $Mg^{2+}$, the second extracted ion. Structural variation in the crown ether phosphonic acid somewhat was influenced to the extraction selectivity in the mixed systems. when variation of the ionized group is influenced in the mixed systems, the selectivity of $Na^+$ as the second extracted ion was much better crown ether carboxylic acid $\underline{1}$ than crown ether phosphonic acid $\underline{2}$, while the efficiency of $Na^+$ extraction was better $\underline{2}$ (83% total loading) than $\underline{1}$ (32%).

• Journal of the Korean Chemical Society
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• v.38 no.5
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• pp.377-381
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• 1994

New bis-crown ethers containing siloxane chain were synthesized. 1,3-Bis(trimethylsiloxy)-1,3-dimethyl-1,3-dipentaoxacyclohexadecamethyl disiloxane (1) was synthesized by reaction of 3-methylene-16-crown-5 (8) with 1,3-bis(trimethylsiloxy)-1,3-dimethyl disiloxane (10) in the presence of Pt catalyst. 1,1,3,3,5,5-Hexamethyl-1,5-dipentaoxacyclohexadecamethyl trisiloxane (2) was synthesized by the reaction of crown ether (8) with 1,1,3,3,5,5-hexamethyl trisiloxane (11) in the presence of Pt catalyst. 3-Methylene-13-crown-4 (7), 3-methylene-16-crown-5 (8), and 3-methylene-19-crown-6 (9) were synthesized by the reaction of triethylene glycol (3), tetraethylene glycol (4), and pentaethylene glycol (5) respectively with 3-chloro-2-chloro-methyl-1-propene (6) in the presence of NaH.