Fluorescence enhancement for alkaloids by anions: Spectroscopic and electrochemical characterizations

Yu Ling Chung, Ruey Ding Hong, Hsiao Wen Wu, Wei Hsiu Hung, Lee Jene Lai, Chong Mou Wang

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Alkaloids such as palmatine and berberine are potential phototoxins, but they exhibit low quantum yields for fluorescence (ΦF). We found that fluoride and hydroxide ions are promising promoters that enhance their values of ΦF in aprotic and aqueous solutions. For example, an increase of ΦF by a factor of 102 was observed when palmatine incorporated 40 equiv TBAF in dimethyl sulfoxide (DMSO). The cause of the enhancement in ΦF was shown to be the interaction of fluoride and hydroxide ions with the quaternary nitrogen atoms contained in the target alkaloid. The effect of substitution of fluoride with other anions such as Cl-, Br-, I-, PF6-, and ClO4- is insignificant. In aqueous media, the efficacy of fluoride and hydroxide ions was greatly reduced. Nevertheless, introducing DNA helped restore the effectiveness of fluoride in enhancing the value of ΦF of alkaloids.

Original languageEnglish
Pages (from-to)85-89
Number of pages5
JournalJournal of Electroanalytical Chemistry
Volume610
Issue number1
DOIs
Publication statusPublished - 2007 Nov 15

Keywords

  • Alkaloid
  • Anion
  • Berberine
  • Fluorescence enhancement
  • Fluoride
  • Palmatine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemical Engineering(all)
  • Electrochemistry

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