Generation of profluorescent isoindoline nitroxides using click chemistry

Morris, Jason C, McMurtrie, John C., Bottle, Steven E., & Fairfull-Smith, Kathryn E. (2011) Generation of profluorescent isoindoline nitroxides using click chemistry. The Journal of Organic Chemistry, 76(12), pp. 4964-4972.

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Novel profluorescent nitroxides bearing a triazole linker between the coumarin fluorophore and an isoindoline nitroxide were prepared in good yields using the coppercatalyzed azide�alkyne 1,3-dipolar cycloaddition reaction (CuAAC). Nitroxides containing 7-hydroxy and 7-diethylamino substitution on their coumarin rings displayed significant fluorescence suppression, and upon reaction with methyl radicals, normal fluorescence emission was returned. The fluorescence emission for the 7-hydroxycoumarin nitroxide and its diamagnetic analogue was found to be strongly influenced by pH with maximal fluorescence emission achieved in basic solution. Solvent polarity was also shown to affect fluorescence emission. The significant difference in fluorescence output between the nitroxides and their corresponding diamagnetic analogues makes these compounds ideal tools for monitoring processes involving free-radical species.

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20 citations in Web of Science®

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ID Code: 43710
Item Type: Journal Article
Refereed: Yes
Additional Information: File saved to I:DRIVE
Keywords: profluorescent isoindoline nitroxides, click chemistry
DOI: 10.1021/jo200613r
ISSN: 0022-3263
Divisions: Past > Schools > Chemistry
Past > QUT Faculties & Divisions > Faculty of Science and Technology
Copyright Owner: Copyright 2011 American Chemical Society
Deposited On: 28 Jul 2011 03:38
Last Modified: 28 Jul 2011 03:38

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