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

Biomedical Sciences Research Institute Computer Science Research Institute Environmental Sciences Research Institute Nanotechnology & Advanced Materials Research Institute

Magri, DC, Callan, JF, de Silva, AP, Fox, DB, McClenaghan, ND and Sandanayake, KRAS (2005) The anthracen-9-ylmethyloxy unit: An underperforming motif within the fluorescent PET (photoinduced electron transfer) sensing framework. JOURNAL OF FLUORESCENCE, 15 (5). pp. 769-775. [Journal article]

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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.

Item Type:Journal article
Faculties and Schools:Faculty of Life and Health Sciences
Faculty of Life and Health Sciences > School of Pharmacy and Pharmaceutical Science
Research Institutes and Groups:Biomedical Sciences Research Institute
Biomedical Sciences Research Institute > Pharmaceutical Science and Practice
ID Code:4073
Deposited By:Professor John Callan
Deposited On:18 Dec 2009 14:43
Last Modified:19 Nov 2012 15:27

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