Journal of Fluorescence

, Volume 15, Issue 5, pp 769-775

First online:

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

  • David C. MagriAffiliated withSchool of Chemistry, Queen’s University
  • , John F. CallanAffiliated withSchool of Chemistry, Queen’s UniversitySchool of Pharmacy, Robert Gordon University
  • , A. Prasanna de SilvaAffiliated withSchool of Chemistry, Queen’s University Email author 
  • , David B. FoxAffiliated withSchool of Chemistry, Queen’s University
  • , Nathan D. McClenaghanAffiliated withLaboratoire de Chimie Organique et Organométallique
  • , K. R. A. Samankumara SandanayakeAffiliated withPhosphagenics R&D Laboratory, Department of Biochemistry and Molecular Biology, Monash University

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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.


Fluorescent sensors ion sensors polarity sensors PET electron transfer