• Mass Spectrometry Letters
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• 제1권1호
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• pp.9-12
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• 2010

Trimethylboroxine (TMB) is a six-membered ring compound containing Lewis acidic boron and Lewis basic oxygen atoms that can bind halide anion and alkali metal cation, respectively. We employed Fourier transform ion cyclotron resonance spectroscopy to study the gas-phase binding of $LiBrLi^+$ and $F^-(KF)_2$ to TMB. TMB forms association complexes with both $LiBrLi^+$ and $F^-(KF)_2$ at room temperature, providing direct evidence for the ditopic binding. Interestingly, the $TMB{\cdot}F^-(KF)_2$ anion complex is formed 33 times faster than the $TMB{\cdot}Li^+BrLi$ cation complex. To gain insight into the ditopic binding of an ion pair, we examined the structures and energetics of $TMB{\cdot}Li^+$, $TMB{\cdot}F^-$, $TMB{\cdot}LiF$ (the contact ion pair), and $Li^+{\cdot}TMB{\cdot}F^-$ (the separated ion pair) using Hartree-Fock and density functional theory. Theory suggests that $F^-$ binds more strongly to TMB than $Li^+$ and the contact ion-pair binding ($TMB{\cdot}LiF$) is more stable than the separated ion-pair binding ($Li^+{\cdot}TMB{\cdot}F^-$).

• Bulletin of the Korean Chemical Society
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• 제27권9호
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• pp.1445-1449
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• 2006

Molecular tweezers based on chenodeoxycholic acid bearing different lengths of arm were synthesized andtheir anion binding affinities were evaluated by $^1H$ NMR, isothermal calorimetric titration, and ESI mass spectrometry. Molecular tweezer 6 showed a high selectivity toward $H_2PO_4\;^-$ over $Cl^-,\;Br^-,\;I^-, $ and $CH_3CO_2\;^-$ by $^1H$ NMR titration, whereas the association constant for $F^-$ revealed the largest value as determined by ITC. The selectivity of 6 towards $F^-$ was about 103 times higher than that of $Cl^-,\;H_2PO_4\;^- $, and $CH_3CO_2\;^-$. ITCexperiment of 6 with $F^-$ in a DMSO showed two binding modes; two sequential association constants $K_1\;=\;2.77\;{\times}\;10^5\;M^{-1}$ and $K_2\;=\;8.68\;{\times}\;10^6\;M^{-1}$ were found. These sequential bindings were confirmed by ESI massspectrometry. 1 : 1 and 1 : 2 complexes of 6 and $F^-$ were found at m/z 868.08 and 884.04.

• Bulletin of the Korean Chemical Society
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• 제30권8호
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• pp.1743-1748
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• 2009

Novel 2-aminothiazolinium based tripodal receptors were designed and synthesized. The binding property of these receptors toward various anions was investigated by the isothermal titration calorimetry (ITC) method. Receptor 4 recognized the acetate anion with 1:1 stoichiometry, whereas it bound the other oxoanions such as sulfate and phosphate in complex modes. By modifying the phenyl groups at the 4-position of the thiazoline rings of the tripodal receptor 4 to induce a mutual aromatic stacking interaction among the three ligands, receptor 10 showed totally different binding behavior, which gave rise to the 1:1 binding mode for the sulfate anion. This result was confirmed by ESI MS spectrometry.

• Bulletin of the Korean Chemical Society
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• 제30권12호
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• pp.3089-3091
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• 2009

• Bulletin of the Korean Chemical Society
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• 제19권10호
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• pp.1133-1136
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• 1998

• Bulletin of the Korean Chemical Society
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• 제21권11호
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• pp.1152-1154
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• 2000

• Bulletin of the Korean Chemical Society
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• 제20권10호
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• pp.1232-1234
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• 1999

• Bulletin of the Korean Chemical Society
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• 제27권5호
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• pp.739-743
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• 2006

Synthesis of cholic acid-based tripodal receptor (1) and its high chloride ion affinity in comparison with that of chenodeoxycholic acid (2) and lithocholic acid-based receptor (3) was achieved. Anion binding affinities of the receptors were evaluated $by\;^1H$ NMR and ITC titrations. Tripodal receptor 1 showed a selective affinity for $CI ^-$ over $Br ^-$, $I^-$, $H_2 PO _4\;^-$, and $CH _3 CO_2\;^-$. The selectivity of 1 for $CI ^-$ is about 3 times that of $Br ^-$, and 17 times that for $H_2 PO_4\;^-$.

• 한국자기공명학회논문지
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• 제25권4호
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• pp.45-50
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• 2021

A calix[4]pyrrole (1) bearing a quaternary ammonium pendant via its meso phenoxy linker has been synthesized as the bromide salt form. It was revealed by ¹H NMR spectroscopic analyses performed in DMSO-d₆ that receptor 1 binds F^- with high affinity and selectivity over other halide anions. The binding of receptor 1•Br^- with F^- and Cltakes place by anion metathesis with the anions including F^- and Cl^-.

• Bulletin of the Korean Chemical Society
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• 제32권spc8호
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• pp.2933-2937
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• 2011

A new highly selective receptor (3) based on an acridine-imidazolium functionalized cholestane for anion sensing was designed and synthesized. A binding study of 3 with various anions was assessed by UV-vis and fluorescence spectroscopies in dry CH3CN. Receptor 3 showed the highest selectivity toward hydrogen pyrophosphate (Ka = $1.5{\times}10^4M^{-1}$).