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Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly

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Abstract

Solid niobium oxides (Nb2O5·nH2O) and niobium phosphate were used as heterogeneous acid catalysts to promote the condensation between a switchable oxazine and a fluorescent coumarin in an aprotic solvent. The catalysts were found to promote the generation of an active methylene from the enamine-based portion of the oxazine, which was followed by a nucleophilic attack on the aldehyde functionality of the coumarin reagent. In the resulting system, the emission of the conjugated fluorophore can be observed at 670 nm and, thus, the processes occurring at the catalyst surface can be monitored in real time by total internal reflection fluorescence microscopy (TIRFM).

Graphical abstract: Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly

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Supplementary files

Article information


Submitted
30 May 2014
Accepted
11 Aug 2014
First published
13 Aug 2014

This article is Open Access

Catal. Sci. Technol., 2015,5, 169-175
Article type
Paper

Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly

S. Impellizzeri, S. Simoncelli, C. Fasciani, M. Luisa Marin, G. L. Hallett-Tapley, G. K. Hodgson and J. C. Scaiano, Catal. Sci. Technol., 2015, 5, 169
DOI: 10.1039/C4CY00703D

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