Journal of Fluorescence

, 15:769

The Anthracen-9-ylmethyloxy Unit: An Underperforming Motif Within the Fluorescent PET (Photoinduced Electron Transfer) Sensing Framework

  • David C. Magri
  • John F. Callan
  • A. Prasanna de Silva
  • David B. Fox
  • Nathan D. McClenaghan
  • K. R. A. Samankumara Sandanayake
Article

DOI: 10.1007/s10895-005-2986-4

Cite this article as:
Magri, D.C., Callan, J.F., de Silva, A.P. et al. J Fluoresc (2005) 15: 769. doi:10.1007/s10895-005-2986-4

Abstract

Compound 2, which was designed to act as a fluorescent sensor for calcium according to the PET (Photoinduced Electron Transfer) principle, shows a relatively small Ca2+-induced fluorescence enhancement factor (FE) of 1.8 whereas its close relative 1 is known to display a far higher FE value of 16. Though designed as fluorescent PET sensors for solvent polarity, compounds 5 and 6 also show negligible fluorescence enhancement as their environments are made progressively less polar even though their relatives 3 and 4 show limiting FE values of 53 and 3, respectively. Indeed, 3 and 4 are useful since they are fluorescent sensors for solvent polarity without being affected by Bronsted acidity. The poor sensory performance of 2, 5, and 6 relative to their cousins is attributed to the presence of an oxygen proximal to the 9-position of an anthracene unit, which opens up a CT (charge transfer) channel. Normal PET sensing service is resumed when the offending oxygen is deleted.

Keywords

Fluorescent sensorsion sensorspolarity sensorsPETelectron transfer

Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  • David C. Magri
    • 1
  • John F. Callan
    • 1
    • 2
  • A. Prasanna de Silva
    • 1
  • David B. Fox
    • 1
  • Nathan D. McClenaghan
    • 3
  • K. R. A. Samankumara Sandanayake
    • 4
  1. 1.School of ChemistryQueen’s UniversityBelfast
  2. 2.School of PharmacyRobert Gordon UniversityAberdeen
  3. 3.Laboratoire de Chimie Organique et OrganométalliqueTalenceFrance
  4. 4.Phosphagenics R&D Laboratory, Department of Biochemistry and Molecular BiologyMonash UniversityVictoriaAustralia