Novel macrocycles with 1,1′-binaphthyl substituents for the recognition of saccharides

Abstract

Novel saccharide-selective receptors 1 and 2 based on a porphyrin with 1,1′-binaphthyl substituents were synthesized and tested for binding of mono-, di- and tri-saccharides; a binding selectivity for di- and tri-saccharides was found.

References

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17. Selected data for 1: δ_H(300 MHZ, CDCl₃) 9.15–8.61 (H, m, Ar), 8.18–7.26 (H, m, Ar), 4.01 (H, m, OCH₃), 2.65 (H, m, OCH₃), –22.41 (s, 2H, NH); m/z(FAB) 1560.5 (MH₂⁺, 100%, calc. for C₁₀₈H₇₈N₄O₈: 1559.8). For 2: m/z(FAB) 1448.5 (MH₂⁺, 100%, calc. for C₁₀₈H₇₂O₁₆: 1447.5). All compounds gave satisfactory elemental analyses. Complexation studies revealed that receptor 1 forms weak H-bonded complexes, while receptor 2 on the other hand showed strong H-bonding donor ability. The complex of 2 with β-D-methylglucopyranose showed a downfield shift of 0.6 ppm with respect to free 2 in CD₃CN; IR showed the strong complexation of the phenolic OH (shift from 3060 to 3100 cm^–1 and from 3300 to 3400 cm^–1) and Raman spectra also indicated the strong complexation (broadening and merging of the multiple peaks in the area of 1460–666 cm^–1).