Weak Affinity Chromatography Using Organic Solvents on Cyanopropyl- and Arene-Modified Silica-Gel Columns®Structural Demands for Host and Guest Moieties and Effect of Solvents
Bulletin of the Chemical Society of Japan, ISSN: 1348-0634, Vol: 96, Issue: 2, Page: 156-167
2023
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Article Description
Weak affinity chromatography (WAC) is effective for isolating target compounds from analogous compounds with similar functional groups. Previously, a few chromatographic behaviors based on WAC using organic solvents were observed in a series of cyclic multiporphyrin systems on cyanopropylmodified silica gel (CN-MS). Here, three cyclic porphyrin trimers with various rigidity were examined on CN-MS to understand the mechanism of the specific interactions between porphyrin derivatives and functional groups on modified silica gel. In addition to CN-MS, six modified silica-gel columns were tested to compare their retention abilities for a cyclic nickel porphyrin dimer (CNiMsCP2). We examined the cosolvent effects of the pyridine eluents for CNiMsCP2. Apparent dissociation constants of CNiMsCP2 with functional groups on the MS columns and effective amounts of the functional groups were estimated by frontal affinity chromatography (FAC). H NMR titrations of acetonitrile and nitrobenzene to CNiMsCP2 were conducted to compare their association constants with movable guest molecules to the dissociation constants with immobilized functional groups obtained in FAC. We found rigidity of cyclic porphyrin derivatives and immobilization of functional groups on silica gel is necessary for significant retentions using WAC. The affinity interaction does not occur at the center of CNiMsCP2, but probably occurs on the surface composed of a bipyridyl moiety and the adjacent edges of the two porphyrins. Polar solvents, such as nitrobenzene, acetonitrile, and methanol, weakened the interaction. Although CNiMsCP2 dissolves well in chloroform, the interactions between CNiMsCP2 and the MS columns are considerably strengthened in the presence of chloroform. The competitiveness of solvents and cosolvents with the interaction of the porphyrin on WAC is independent of the solubility of the analyte.
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