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https://hdl.handle.net/2440/17916
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Type: | Journal article |
Title: | A preparative and preliminary spectroscopic study of analogues of a zinquin-related fluorophore |
Author: | Kimber, M. Geue, J. Lincoln, S. Ward, A. Tiekink, E. |
Citation: | Australian Journal of Chemistry: an international journal for chemical science, 2003; 56(1):39-44 |
Publisher: | C S I R O Publishing |
Issue Date: | 2003 |
ISSN: | 0004-9425 1445-0038 |
Statement of Responsibility: | Marc C. Kimber, Jason P. Geue, Stephen F. Lincoln, A. David Ward and Edward R. T. Tiekink |
Abstract: | <jats:p>The syntheses of the 4- and 5-methoxy isomers of 4-N-(6-methoxy-2-methyl-8-quinolyl)-4-methylbenzenesulfon-amide and of N-(2-methoxy-8-quinolyl)-4-methylbenzenesulfonamide are described. The 6-methoxy compound is a precursor of Zinquin ester, a specific fluorophore for Zn(II). The 2-methoxy analogue was synthesized by nitration of 2-chloroquinoline and subsequent functional group manipulation. The 4-methoxy isomer was synthesized from a 4-quinolone derivative, and the 5-methoxy isomer was synthesized by a standard Skraup quinoline synthesis. The structures of the 4- and 5-methoxy isomers were determined by single-crystal X-ray analysis. All of these compounds showed a bathochromic shift in their ultraviolet/visible spectra upon addition of Zn(II) to the solution. These compounds are all weakly or non-fluorescent in solution. All form fluorescent complexes with Zn(II) except the 5-methoxy compound. The 4-methoxy compound forms a significantly more fluorescent complex than those of the 6-methoxy compound and Zinquin ester and has a higher quantum yield than the others.</jats:p> |
Rights: | © CSIRO 2003 |
DOI: | 10.1071/CH01071 |
Published version: | http://dx.doi.org/10.1071/ch01071 |
Appears in Collections: | Aurora harvest 6 Chemistry publications Environment Institute publications |
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