• Bulletin of the Korean Chemical Society
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• 제17권6호
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• pp.502-506
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• 1996

Several ester group-containing calix[4]arenes were synthesized by the reaction of calix[4]arene and various acyl chlorides. Two or four ethyl succinyl units could be introduced into the calix[4]arene lower rim depending on the reaction conditions. But the mixture of three and four ethyl malonyl substituted calix[4]arenes were obtained and only three ethyl oxalyl units were introduced at the lower rim of calix[4]arene. Interestingly when calix[4]arene was treated with ethyl oxalyl chloride in the presence of aluminum chloride, two ethyl oxalyl units were introduced at the upper rim of calix[4]arene. The conformation of those ester-containing calix[4]arenes was presented based on the 1H and 13C NMR spectra.

• Bulletin of the Korean Chemical Society
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• 제19권7호
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• pp.770-776
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• 1998

Several ABCH type chiral calix[4]arenes were prepared from monoalkyl calix[4]arenes by treating with various acyl halide, followed by reacting with benzoyl chloride in pyridine. These asymmetrically substituted ABCH type calix[4]arenes are obtained as racemates mixture which are confirmed by the chiral shift reagent in 1H NMR spectra. The molecular and crystal structure of 5-nitro-26-allyloxy-25-benzoyloxy-28-isobutyryloxy-27-hydroxycalix[4]arene 8a has been determined by the X-ray diffraction method. Two independent enantiomeric molecules are crystallized in a 1: 1 racemate mixture. They are in the partial cone conformation in which the benzoyloxy phenyl group is down. There is a bifurcated intramolecular hydrogen bonding involving three functional groups in each molecule.

• Bulletin of the Korean Chemical Society
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• 제17권6호
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• pp.525-528
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• 1996

Seven cali[4]arenes, having two different substituents in AAAB or AABB pattern at the upper rim of calix were synthesized by fragmentation condensation reaction of p-substituted phenol trimer (AAA) with 2,6-bishydroxymethylated 4-substituted phenol (B) or that of dimer (AA) with 2,2'-bishydroxymethylated dimer (BB). An equimolar mixture of the coupling components (trimer and monomer or dimer and dimer) was refluxed in dioxane in the presence of TiCl4to afford calix[4]arene 6 and 7 in 15-38% yield. The structure of calix[4]arenes was confirmed by elemental analysis and the 1H/13C NMR spectroscopy.

• Bulletin of the Korean Chemical Society
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• 제16권11호
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• pp.1122-1125
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• 1995

Three inherently chiral calix[4]arenes 3-5 were synthesized as racemate starting from the ethylation at 1.3-distal hydroxy groups of calix[4]arene 2 which has two phenyl groups at upper rim in AABB fashion, and then two remaining hydroxy groups were acetylated by treatment with acetyl chloride in the presence of NaH to produce calix[4]arene 4. Treatment of 4 with AlCl3 under Fries rearrangement conditions, only one acetyl group was rearranged to the para-position to afford calix[4]arene 5 with AABC substitution pattern at the upper rim of calix. The structure of chiral calix[4]arenes were confirmed based on NMR and massspectra.

• Bulletin of the Korean Chemical Society
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• 제18권4호
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• pp.409-415
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• 1997

Several calixarene derivatives of 5,11,17,23-tetra-tert-butyl-25-(3,5-dinitrobenzoyloxy)-26,27,28-trihydroxycalix[4]arene 2 were synthesized by the reaction of 2 with several acyl and alkylating agents in the presence of base such as pyridine and K2CO3 in THF. Acylation of monobenzoylated p-tert-butylcalix[4]arene 2 yielded their corresponding 1,3-diacylated calix[4]arenes 3a-3g. On the other hand, alkylation of 2 produced a variety calix[4]arene derivatives such as 1,2- and 1,3-disubstituted calix[4]arenes 4a-4c, 4e-4f, or 1,2,4-trisubstituted calix[4]arene 4d. 1,2-Disubstituted calix[4]arenes are chiral. All derivatives exist as a cone conformation based on NMR studies.

• Bulletin of the Korean Chemical Society
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• 제22권12호
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• pp.1345-1349
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• 2001

New quadruply-bridged calix[6]arenes (I-V) have been studied as cesium selective ionophores in poly(vinyl chloride) (PVC) membrane electrodes. PVC membranes were prepared with dioctyl sebacate (DOS) or 2-nitrophenyl octyl ether (o-NPOE) as the sol vent mediator and potassium tetrakis(p-chlorophenyl)borate as the lipophilic salt additive. These ionophores produced electrodes with near-Nernstian slope. The selectivity coefficients for cesium ion with respect to alkali, alkaline earth and ammonium ions have been determined. The lowest detection limit (logaCs+ = -6.3) and the higher selectivity coefficient (logkpotCs+,Rb+ = -2.1 by SSM, -2.3 by FIM for calix[6]arene I) for Cs+ have been obtained for membranes containing quadruply-bridged calix[6]arenes (I, Ⅱ, Ⅲ), which have no para t-butyl substituents on the bridging benzene ring.

• Bulletin of the Korean Chemical Society
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• 제19권1호
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• pp.132-134
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• 1998

• Bulletin of the Korean Chemical Society
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• 제22권1호
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• pp.100-102
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• 2001

• 대한화학회지
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• 제36권6호
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• pp.933-940
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• 1992

Calix[6]arene을 포름알데히드와 이차아민과 반응시키면 물에 녹는 칼릭세린 염기가 얻어진다. 이를 메틸요오드로 처리하여 암모늄 염을 만들고 다양한 친핵성 물질과 반응시키면 칼릭세린의 파라위치에 작용기가 포함된 calix[6]arene이 얻어진다. Calix[6]arene도 포름알데히드와 이차의 아릴아민과 반응시켜 물에 녹는 칼릭세린 아민을 만들었다. 이렇게 합성된 칼릭세린중 물에 녹는 아민과 산기가 포함된 calix[6]arene과 calix[8]arene을 운반체로 이용하여 중성의 방향족 물질들을 통과시키는 연구를 U 형태의 유리관을 이용하여 수행하였다. 방향족 기질들로는 나프탈렌, 안트라센, 파이렌, 풀우란텐 등의 고체물질을 사용하였다.

• Bulletin of the Korean Chemical Society
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• 제19권3호
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• pp.279-281
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• 1998