View : 34 Download: 0

Facile dimerization and circular dichroism characteristics of 6-O-(2-sulfonato-6-naphthyl)-β-cyclodextrin

Title
Facile dimerization and circular dichroism characteristics of 6-O-(2-sulfonato-6-naphthyl)-β-cyclodextrin
Authors
Park J.W.Song H.E.Lee S.Y.
Ewha Authors
박준우
SCOPUS Author ID
박준우scopusscopus
Issue Date
2002
Journal Title
Journal of Physical Chemistry B
ISSN
1089-5647JCR Link
Citation
vol. 106, no. 20, pp. 5177 - 5183
Indexed
SCOPUS WOS scopus
Abstract
A monofunctional derivative of β-cyclodextrin (β-CD) containing a 2-sulfonato-6-naphthyl group at the primary face (1: β-CD-NS) was prepared. The concentration dependences of fluorescence, circular dichroism (c.d.), and NMR spectra of 1 have been investigated and compared with the spectral changes associated with complexation of 6-methoxy-2-naphthalenesulfonate (MNSS) with β-CD. When the concentration of 1 was increased, the following were observed: the enhancement of the concentration-normalized fluorescence intensity; an increase in molar ellipticities of the negative band around 280 nm; a more pronounced exciton coupling band around 230 nm in c.d. spectra; and an upfield shift of NMR signals from aromatic protons. The concentration dependent fluorescent intensity and molar ellipticity data fitted well to the monomerdimer equilibrium of 1 with the dimerization constant of 9700 ± 2500 M -1. The dimerization constant is much larger than the association constants of MNSS with β-CD (510 ± 40 M -1) and 1 with β-CD (430 ± 50 M -1). The naphthyl groups in the dimer do not show an excimer band in fluorescence spectra but exhibit exciton coupling bands around 230 and 330 nm. These indicate that 1 forms a head-to-head type dimer, which is stabilized by mutual inclusion of the 2-sulfonato-6-naphthyl moieties deeply into β-CD cavities of counter molecules. The naphthyl moiety of the monomer of 1 is in a similar environment to that in a 1/noctyl sulfate complex and appears to cap the primary face of β-CD loosely. Compared to the c.d. spectrum of the MNSS/β-CD complex, the spectrum of the 1/β-CD complex is similar in shape, but the rotational strengths of the c.d. bands are much greater.
DOI
10.1021/jp014191j
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE