TY - JOUR
T1 - Structural aspects of marked difference in intramolecular exciplex emissions from self-complexes of β-cyclodextrins modified with (R) or (S)-1-(1-aminoethyl)naphthalene
AU - Suzuki, Iwao
AU - Kato, Yuki
AU - Egawa, Yuya
AU - Anzai, Jun ichi
AU - Wadamori, Makoto
AU - Yokomizo, Hideki
AU - Takahashi, Keiko
N1 - Funding Information:
We are grateful to Yamakawa Yakuhin Kogyo Co. Ltd., for the generous gift of the optically pure forms of 1-(1-aminoethyl)naphthalene. This work was partly supported by a Grant-in-Aid (11780411) from the Ministry of Education, Science, Sports and Culture, Japan. One of the authors (I.S.) also gratefully appreciates the Mitsubishi Chemical Foundation for their financial support in part.
PY - 2002/1/9
Y1 - 2002/1/9
N2 - Novel β-cyclodextrin (β-CyD) derivatives having an (R) or (S)-1-(1-aminoethyl)-naphthyl group exhibited red-shifted and structureless fluorescence and the normal fluorescence of the naphthyl group in alkaline aqueous solutions. The red-shifted fluorescence is attributed to the intramolecular exciplex. The intensity of the exciplex fluorescence is dependent on the chirality of the naphthyl group; the (S)-isomer emitted a stronger exciplex fluorescence than the (R)-isomer. From the NMR and circular dichroism spectral studies, the conformation of the intramolecular complexes of the (R)- and (S)-isomers is suggested; the naphthyl group of the (S)-isomer exists outside the β-CyD cavity, while the (R)-isomer is in the cavity. This conformational difference provides in the difference in the intramolecular exciplex formation.
AB - Novel β-cyclodextrin (β-CyD) derivatives having an (R) or (S)-1-(1-aminoethyl)-naphthyl group exhibited red-shifted and structureless fluorescence and the normal fluorescence of the naphthyl group in alkaline aqueous solutions. The red-shifted fluorescence is attributed to the intramolecular exciplex. The intensity of the exciplex fluorescence is dependent on the chirality of the naphthyl group; the (S)-isomer emitted a stronger exciplex fluorescence than the (R)-isomer. From the NMR and circular dichroism spectral studies, the conformation of the intramolecular complexes of the (R)- and (S)-isomers is suggested; the naphthyl group of the (S)-isomer exists outside the β-CyD cavity, while the (R)-isomer is in the cavity. This conformational difference provides in the difference in the intramolecular exciplex formation.
KW - Cyclodextrin derivatives
KW - Fluorescence spectroscopy
KW - Intramolecular exciplex emission
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U2 - 10.1016/S0022-2860(01)00681-0
DO - 10.1016/S0022-2860(01)00681-0
M3 - Article
AN - SCOPUS:0037045285
VL - 602-603
SP - 223
EP - 231
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
SN - 0022-2860
ER -