Chiral recognition of ephedrine: Hydrophilic polymers bearing β-cyclodextrin moieties as chiral sensitive host molecules

Abstract

SummaryIn this work we demonstrate chiral recognition of (+)- and (−)-ephedrine using a cyclodextrin-containing polymer. The supramolecular structures obtained by complexation of ephedrine and cyclodextrin were verified by 2-D ROESY NMR measurements. Dynamic light scattering showed clear differences in the mean coil size.

Triple Thermoresponsiveness of a TADDOL-Based Homopolymer through the Formation of Supramolecular Complexes with Chiral Guest Molecules at Variable Ratios

“…29 They also used β-CD as the effector to exhibit LCST-type and UCST-type phase transition of polymer solution. 30,31 Moreover, PNiPAm shows tunable clouding points of LCST-type phase separation in the presence of alkyl alcohols in aqueous solution, 32 and the fundamental basis is the same with that of Ritter's systems. Our group extended this strategy for controlling the thermoresponsiveness of the polymer solution in various nonaqueous media.…”

“…As the pseudo-solvating compounds, the effectors can form the supramolecular complexes with the polymer chain and have enough compatibility to solubilize the polymer chain. , As the pioneering work, Ritter et al showed that the polymers tethering adamantyl groups and β-cyclodextrins (β-CD) complexes exhibited LCST-type phase transition induced by the dissociation of the polymer complexes with β-CD and the aggregation of the adamantyl groups in aqueous solution . They also used β-CD as the effector to exhibit LCST-type and UCST-type phase transition of polymer solution. , Moreover, PNiPAm shows tunable clouding points of LCST-type phase separation in the presence of alkyl alcohols in aqueous solution, and the fundamental basis is the same with that of Ritter’s systems. Our group extended this strategy for controlling the thermoresponsiveness of the polymer solution in various nonaqueous media.…”

Chiral recognition of enantiomeric isobornyl methacrylate‐containing hydrogels with α‐cyclodextrin

“…14,15 A chiral recognition of enantiomeric phenylalanine moieties in polymers with cyclodextrins was achieved by our group. 16 Thus, a differentiation of chiral components in polymers using cyclodextrin is possible. To the best of our knowledge, the enantioselective behaviour of cyclodextrin towards camphor and its derivatives has not been transferred to the field of polymer chemistry and thereby macroscopic effects.…”

Molecular Recognition: Influence of Para‐Versus‐Meta‐Substituted Phenyl Moieties on the Swelling Degree of Macroscopic Polymeric Gels in Aqueous Cyclodextrin Solutions

“…Accordingly, molecular recognition of low‐ and high‐molecular‐weight organic substrates via host–guest complexes gained a lot of interest in the last decades . As an example, the use of cyclodextrins (CDs) for gel‐to‐gel attraction in the mm scale has been described .…”

“…[2][3][4][5] Accordingly, molecular recognition of low-and highmolecular-weight organic substrates via host-guest complexes gained a lot of interest in the last decades. [6][7][8][9][10] As an example, the use of cyclodextrins (CDs) for gel-to-gel attraction in the mm scale has been described. [ 11 ] Furthermore, CDs have been used for the formation of smart hydrogels by self-assembly of star-shaped supramolecular architectures [ 12 ] and the transition of nanogel-like micelles to nanovesicles.…”