K. Hamasaki et al., DANSYL-MODIFIED CYCLODEXTRINS AS FLUORESCENT CHEMOSENSORS FOR MOLECULAR RECOGNITION, Supramolecular chemistry, 8(2), 1997, pp. 125-135
alpha-, beta-, and gamma-cyclodextrin derivatives (cyclodextrin is abb
reviated as CD, hereafter) bearing an dansyl or dansylglycine moiety a
t the primary or secondary side of CD were synthesized as fluorescent
indicators for molecular recognition. The CDs with the moiety at the s
econdary hydroxy side have an asymmetric cavity with a distorted CD fr
amework because of the conversion of one glucose member to an altrose
residue and the effects of this distortion of the CD ring on the sensi
ng abilities were examined, compared with the case of symmetrical CDs
bearing the dansyl moiety at the primary side. The results demonstrate
that the asymmetrical CDs are unfavorable to accommodate the guest sp
ecies due to the cavity narrowed by the distortion, contrasting with t
he observation that the symmetrical CDs exhibit remarkable sensing abi
lities for various guests.