Dodecaborate-Functionalized Anchor Dyes for Cyclodextrin-Based Indicator Displacement Applications

Dodecaborate-Functionalized Anchor Dyes for Cyclodextrin-Based Indicator Displacement Applications

A new type of water-soluble anchor dyes, that is, dyes which carry an auxiliary unit for strong binding to macrocyclic host molecules, has been synthesized. It consists of 7-nitrobenzofurazan (NBD) as a dye and the dodecaborate cluster (B12H11R) as a dianionic, globular, and purely inorganic anchori...

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Veröffentlicht in:Organic letters 2016-03, Vol.18 (5), p.932-935
Hauptverfasser: Assaf, Khaleel I, Suckova, Olga, Al Danaf, Nader, von Glasenapp, Victoria, Gabel, Detlef, Nau, Werner M
Format: Artikel
Sprache:eng
Schlagworte:
Boron Compounds - chemistry
Cyclodextrins - chemistry
Fluorescence
Fluorescent Dyes - chemistry
Molecular Structure
Oxadiazoles - chemistry
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Zusammenfassung:A new type of water-soluble anchor dyes, that is, dyes which carry an auxiliary unit for strong binding to macrocyclic host molecules, has been synthesized. It consists of 7-nitrobenzofurazan (NBD) as a dye and the dodecaborate cluster (B12H11R) as a dianionic, globular, and purely inorganic anchoring group for cyclodextrins (K a > 105 M–1). The synthesized dodecaborate-substituted dyes show marked changes in their photophysical properties (UV–vis and fluorescence) upon complexation with cyclodextrins (β-CD and γ-CD), such that the resulting host·dye complexes (1:1 stoichiometry) present sensitive reporter pairs for indicator displacement applications.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03611