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Synfacts 2010(5): 0531-0531  
DOI: 10.1055/s-0029-1219681
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Phenanthroline-Porphyrin Hybrid as a Fluorescence Sensor for Magnesium(II)

Contributor(s):Timothy M. Swager, William R. Collins
M. Ishida, Y. Naruta*, F. Tani
Kyushu University, Fukuoka, Japan
A Porphyrin-Related Macrocycle with an Embedded 1,10-Phenanthroline Moiety: Fluorescent Magnesium(II) Ion Sensor
Angew. Chem. Int. Ed.  2010,  49:  91-94  
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Publication History

Publication Date:
22 April 2010 (online)

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Key words

chemosensors - porphyrins - magnesium sensing

Significance

The selective detection of magnesium ions in the presence of sodium, potassium and calcium is particularly important in elucidating biological processes. Porphyrins and their derivatives possess both a far-red fluorophore and a binding domain for sensing. Unfortunately, porphyrins almost exclusively sense anions. The authors demonstrate that the novel 1,10-phenanthroline-phenyldipyrromethane hybrid macrocycle can effectively bind magnesium cations. Upon binding, the macrocycle undergoes a red shift as well as a 16-fold enhancement in emission intensity. The binding studies were also performed in an aqueous medium to demonstrate applicability for biological systems.

Comment

The currently available molecular fluorescent probes for magnesium suffer from other cation interference. The authors demonstrate that this novel macrocycle binds calcium very weakly and effectively not at all sodium or potassium.

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