New synthetic strategies for xanthene-dye-Appended cyclodextrins

Milo Malanga, Andras Darcsi, Mihaly Balint, Gabor Benkovics, Tamas Sohajda, Szabolcs Beni

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

Keywords

  • DMT-MM
  • Fluorescein
  • Rhodamine
  • Supramolecular Assembly

ASJC Scopus subject areas

  • Organic Chemistry

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