ABSTRACT
Correction for 'Room-temperature phosphorescent γ-cyclodextrin-cucurbit[6]uril-cowheeled [4]rotaxanes for specific sensing of tryptophan' by Xingke Yu et al., Chem. Commun., 2019, 55, 3156-3159.
ABSTRACT
Room temperature phosphorescent (RTP) γ-CD-CB[6]-cowheeled [4]rotaxanes were synthesized by implanting a naphthalene axle into the cavity of iodine-substituted γ-CDs. The strong green RTP was quenched exclusively by Trp while no RTP quenching was observed with other major physiological amino acids or with the Trp-containing protein HSA, demonstrating a highly specific sensing of free Trp.
Subject(s)
Bridged-Ring Compounds/chemistry , Imidazoles/chemistry , Luminescent Agents/chemistry , Rotaxanes/chemistry , Tryptophan/analysis , gamma-Cyclodextrins/chemistry , Bridged-Ring Compounds/chemical synthesis , Humans , Imidazoles/chemical synthesis , Luminescent Agents/chemical synthesis , Luminescent Measurements/methods , Rotaxanes/chemical synthesis , Temperature , Tryptophan/blood , gamma-Cyclodextrins/chemical synthesisABSTRACT
A biphenyl photosensitizer axle was implanted into the cavities of native and capped γ-cyclodextrins through rotaxanation using a cucubit[6]uril-templated azide-alkyne 1,3-dipolar cycloaddition, resulting in the construction of highly defined chiral binding/sensitizing sites. The orientation and interaction of the axle and capping moieties at the ground and excited states were interrogated by NMR, UV-vis, circular dichroism, and fluorescence spectroscopic studies. In situ photoisomerization of (Z,Z)-1,3-cyclooctadiene sensitized in the cavity of these [4]rotaxanes afforded (Z,E)-1,3-cyclooctadiene in up to 15.3% ee, which represents the highest level of enantiodifferentiation obtained to date for this supramolecular photochirogenesis.
ABSTRACT
The (P)- and (M)-3-azonia[6]helicenyl ß-cyclodextrins exhibit L/D selectivities of up to 12.4 and P/M preferences of up to 28.2 upon complexation with underivatized proteinogenic amino acids in aqueous solution at pH 7.3.
