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- W3048480177 abstract "Abstract The host‐guest chemistry and applications of cyclodextrins in aqueous media is well established. However, a comprehensive study in organic solvents is lacking. Here, we report the design and synthesis of 6‐ O ‐ tert ‐butyldimethylsilylated β‐cyclodextrin (TBDMS‐β‐CD) bearing various aromatic substitutions at the 2‐ O position and their inclusion complex formation with aromatic guests in nonpolar organic solvents. Compared to the parent TBDMS‐β‐CD, these derivatives exhibit at least a 10‐fold increase in inclusion ability toward pyrene through cooperative guest binding with the CD cavity and the aromatic substituents at the 2‐ O position. The type of the aromatic substituent largely affects the chiral recognition ability of TBDMS‐β‐CD toward 1‐(1‐naphthyl)ethylamine in cyclohexane. A TBDMS‐β‐CD derivative with a p ‐tolyl substituent has a remarkable chiral selectivity for the ( S )‐1‐(1‐naphthyl)ethylamine over the corresponding ( R )‐isomer ( K S /K R =4.1±0.5), whereas a TBDMS‐β‐CD derivative with a 2‐picolyl substituent shows the inverse chiral selectivity ( K R /K S =8.7±0.6)." @default.
- W3048480177 created "2020-08-18" @default.
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- W3048480177 date "2020-08-01" @default.
- W3048480177 modified "2023-09-26" @default.
- W3048480177 title "Control of Guest Inclusion and Chiral Recognition Ability of 6‐ <i>O</i> ‐Modified β‐Cyclodextrins in Organic Solvents by Aromatic Substituents at the 2‐ <i>O</i> Position" @default.
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- W3048480177 doi "https://doi.org/10.1002/cplu.202000522" @default.
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