Synthesis and spectroscopic properties of benzo- and naphthofuryl-3-hydroxychromones


Klymchenko A., Ozturk T. , PIVOVARENKO V., DEMCHENKO A.

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, vol.79, no.4, pp.358-363, 2001 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 79 Issue: 4
  • Publication Date: 2001
  • Doi Number: 10.1139/cjc-79-4-358
  • Title of Journal : CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
  • Page Numbers: pp.358-363

Abstract

With the focus of designing new fluorescent probes, four new 3-hydroxy-chromone derivatives bearing benzofuran and naphthofuran groups were synthesized. They show bathochromic absorption shifts relative to 3-hydroxyflavone with the ability of retention to display the excited-state proton transfer. Disruption of the planarity by the methyl group in the furan ring leads to a decrease of both the extinction coefficient and the contribution of long wavelength absorption band, while molecules without a methyl group showed two distinct absorption bands. Shifts to longer wavelengths are also observed in fluorescent spectra, and the absence of the methyl group results in a dramatic increase of fluorescence quantum yield and lifetime. Of the extended 3-hydroxychromone derivatives, 3-hydroxy-2-naphtho[2,1-b]furan-2-yl-chromone has shown comparable, and in some cases better, absorption and fluorescence properties than the 3-hydroxychromones synthesized so far, which make it a highly promising candidate as molecular probe for analytical chemistry, biophysics, and cellular biology.