Cooperative molecular recognition of dyes by two bis(β-cyclodextrin)s with aromatic, sulfur-containing, diamine tethers

Cooperative molecular recognition of dyes by two bis(β-cyclodextrin)s with aromatic,... The molecular binding behavior of two bis(β-cyclodextrin (CD))s, that is, 4,4′-diaminodiphenylsulfone-bridged bis(β-CD) 2 and 4,4′-diaminodiphenyldisulfide-bridged bis(β-CD) 3 with some representative organic dyes, i.e., acridine red (AR), neutral red (NR), ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 2-(p-toluidinyl)naphthalenesulfonate (TNS), rhodamine B (RhB), and brilliant green (BG), has been investigated at 25 °C in phosphate buffer (pH 7.20) by ultraviolet, fluorescence and 2D NMR spectroscopy. The fluorescence of ANS, TNS, AR, and NR are enhanced, whereas that of RhB is quenched, by inclusion complexation with both host compounds. The results obtained show bridged bis(β-CD)s 2 and 3 with dye guests give higher complex stability constants (K S) than those of the native β-CD 1, through cooperative binding of two hydrophobic CD cavities with one guest. In addition, the K S values of all guests with host 3 are much larger than those with 2 except for NR as guest. The 2D 1H NOESY spectrum of host 3 and RhB was acquired to confirm the cooperative binding mode. The molecular binding ability of dyes by hosts 1–3 are discussed from the viewpoint of the size and shape-fitting relationship between host and guest. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Cooperative molecular recognition of dyes by two bis(β-cyclodextrin)s with aromatic, sulfur-containing, diamine tethers

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Publisher
Springer Netherlands
Copyright
Copyright © 2010 by Springer Science+Business Media B.V.
Subject
Chemistry; Inorganic Chemistry ; Physical Chemistry ; Catalysis
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-010-0227-1
Publisher site
See Article on Publisher Site

Abstract

The molecular binding behavior of two bis(β-cyclodextrin (CD))s, that is, 4,4′-diaminodiphenylsulfone-bridged bis(β-CD) 2 and 4,4′-diaminodiphenyldisulfide-bridged bis(β-CD) 3 with some representative organic dyes, i.e., acridine red (AR), neutral red (NR), ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 2-(p-toluidinyl)naphthalenesulfonate (TNS), rhodamine B (RhB), and brilliant green (BG), has been investigated at 25 °C in phosphate buffer (pH 7.20) by ultraviolet, fluorescence and 2D NMR spectroscopy. The fluorescence of ANS, TNS, AR, and NR are enhanced, whereas that of RhB is quenched, by inclusion complexation with both host compounds. The results obtained show bridged bis(β-CD)s 2 and 3 with dye guests give higher complex stability constants (K S) than those of the native β-CD 1, through cooperative binding of two hydrophobic CD cavities with one guest. In addition, the K S values of all guests with host 3 are much larger than those with 2 except for NR as guest. The 2D 1H NOESY spectrum of host 3 and RhB was acquired to confirm the cooperative binding mode. The molecular binding ability of dyes by hosts 1–3 are discussed from the viewpoint of the size and shape-fitting relationship between host and guest.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Dec 8, 2010

References

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