A C3 symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral stationary phase (CSP) and three C2 symmetric (R)-phenylglycinol CSPs were newly synthesized using o-, m-, and p-phthaloyl dichlorides. These CSPs were used to compare the resolution of 25 chiral samples using a previously reported 3,5-dinitrobenzoyl (R)-phenylglycinol-derived CSP. Even though all CSPs have the same chiral moiety, the C3 symmetric CSP showed the best resolution.
A two-dimensional chiral open framework, [Ni(L(R,R))](3)[C(6)H(3)(COO)(3)](2).12H(2)O.CH(3)CN (3), is prepared from a nickel(II) macrocyclic complex with chiral pendants and benzenetricarboxylate in MeCN/H(2)O and characterized [L(R,R) = 1,8-bis[(R)-alpha-methylbenzyl]-1,3,6,8,10,13-hexaazacyclotetradecane]. The open framework shows selective chiral recognition by interactions between the solid 3 and rac-1,1'-bi-2-naphthol.
Cyclodextrin (CD) polymers were synthesized from the reaction of native CDs with a hexamethylene diisocyanate (HDI) compound in a dried DMF solution. The obtained CD polymer contained a range of 8 -14% N due to HDI by elemental analysis. The physical and chemical properties of the CD polymers were characterized by IR, solid state 13 C NMR, TGA, and DSC, respectively. An HPLC column was prepared using the CD polymer with a carbamate linker by a slurry method. Separation of the phenol isomers was conducted using the CD polymer stationary phase and CD by HPLC. Furthermore, an inclusion complex of the phenol isomer was studied by FT-Raman spectroscopy. From the HPLC and FT-Raman results, inclusion phenomena of o-, m-, and p-nitrophenol onto CD and CD polymers were analyzed.
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