New synthetic strategies for xanthene-dye-Appended cyclodextrins

Milo Malanga, Andras Darcsi, Mihaly Balint, Gabor Benkovics, Tamas Sohajda, S. Béni

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Xanthene dyes can be appended to cyclodextrins via an ester or amide bridge in order to switch the fluorescence on or off. This is made possible through the formation of nonfluorescent lactones or lactams as the fluorophore can reversibly cyclize. In this context we report a green approach for the synthesis of switchable xanthene-dye-appended cyclodextrins based on the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). By using 6-monoamino-β-cyclodextrin and commercially available inexpensive dyes, we prepared rhodamine- and fluorescein-appended cyclodextrins. The compounds were characterized by NMR and IR spectroscopy and MS spectrometry, their UV-vis spectra were recorded at various pH, and their purity was determined by capillary electrophoresis. Two potential models for the supramolecular assembly of the xanthene-dyeappended cyclodextrins were developed based on the set of data collected by the extensive NMR characterization.

Original languageEnglish
Pages (from-to)537-548
Number of pages12
JournalBeilstein Journal of Organic Chemistry
Volume12
DOIs
Publication statusPublished - Mar 17 2016

Fingerprint

Xanthenes
Cyclodextrins
Coloring Agents
Lactams
Capillary electrophoresis
Rhodamines
Fluorophores
Coupling agents
Lactones
Fluorescein
Amides
Spectrometry
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Esters
Fluorescence
Switches
Nuclear magnetic resonance

Keywords

  • DMT-MM
  • Fluorescein
  • Rhodamine
  • Supramolecular Assembly

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

New synthetic strategies for xanthene-dye-Appended cyclodextrins. / Malanga, Milo; Darcsi, Andras; Balint, Mihaly; Benkovics, Gabor; Sohajda, Tamas; Béni, S.

In: Beilstein Journal of Organic Chemistry, Vol. 12, 17.03.2016, p. 537-548.

Research output: Contribution to journalArticle

Malanga, Milo ; Darcsi, Andras ; Balint, Mihaly ; Benkovics, Gabor ; Sohajda, Tamas ; Béni, S. / New synthetic strategies for xanthene-dye-Appended cyclodextrins. In: Beilstein Journal of Organic Chemistry. 2016 ; Vol. 12. pp. 537-548.
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