
TY  - JOUR
A1  - Kimber, Marc C. 
A1  - Geue, Jason P. 
A1  - Lincoln, Stephen F. 
A1  - Ward, A. David 
A1  - Tiekink, Edward R. T. 
T1  - A Preparative and Preliminary Spectroscopic Study of Analogues of a Zinquin-Related Fluorophore
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2003
VL  - 56
IS  - 1
SP  - 39
EP  - 44
KW  - 
UR  - https://doi.org/10.1071/CH01071 
N2  - 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. 
ER  -

