The anthracen-9-ylmethyloxy unit: An underperforming motif within the fluorescent PET (photoinduced electron transfer) sensing framework

DC Magri, JF Callan, AP de Silva, DB Fox, ND McClenaghan, KRAS Sandanayake

Research output: Contribution to journalArticle

34 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)769-775
JournalJournal of Fluorescence
Volume15
Issue number5
DOIs
Publication statusPublished - Sep 2005

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